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A Big Little Move (by Dana/DrLefty)

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AUTHOR: DrLefty on 3/28/2026

A couple of years ago, as I started to plan my retirement, I published an article called “When and Where?” Later, I followed up with a post explaining that I’d chosen the “when” (July 1, 2025) and that my husband and I were still thinking about the “where” but were inclined to stay put in the college town in Northern California where we’ve lived for almost 35 years.

One option we’ve been seriously considering is purchasing a home for ourselves with a floor plan that could accommodate our adult daughter, who’s struggled with unemployment and underemployment, if she runs out of options at some point. Our three-bedroom condo, while it has a guest bedroom and bathroom, is not really laid out well for long-term success in multigenerational living.

So for a while (going back as far as fall 2024), we’ve been looking around our area, specifically at homes with Accessory Dwelling Units (ADU) or with a separate wing or even downstairs ensuite bedroom with an upstairs–something that would allow some separation and privacy for all of us. But we wanted the home to be something we would like, too, and that would fit within our financial parameters. We signed up with a buyer’s agent in fall 2025 and got pre-approved for a new mortgage so that we could move quickly in case we found that perfect unicorn property.

We had almost given up on the idea of finding the right place in the town where we live. The housing market is tight and there just aren’t tons of options. We looked and looked at open houses and with our agent, but nothing seemed right–until one month ago today.

A house was listed on February 26. I saw the listing and our agent texted us about it, too. I wasn’t initially that excited. It has an ADU and it’s in a very desirable part of town, but it was old (more on that below), and, I thought, priced a bit high. But on February 28, we went out to lunch and then my husband said, “Is there an open house today?” There was, we went to it, came home, and my husband looked at me and said, “That checks all the boxes.” We texted our agent and went back with him the next day. He explained that given how popular that particular neighborhood is in our town, the property wasn’t actually overpriced. A few days later, we made an offer, actually bidding a bit under the asking price on our agent’s suggestion. The sellers countered, still below asking price. Our agent said it was a great deal and we should grab it. We were literally at a baseball game in Scottsdale, Arizona, when he called and said “Get on your phones NOW and accept the offer before the sellers get another one!”

So…we’re now buying a house and getting ready to sell our condo. We close on the house on April 6 and agreed to let the seller stay another month, so we’ll move there in the second week of May. I’m sort of out of breath at how quickly this is all happening. Even though we were looking/pre-approved, we’d just about given up on the idea, and our agent even admitted he didn’t think we were going to find something.

Here are the pros and cons of what we’re doing:

  • The house is only about a mile from where we live now, but it’s closer to downtown, campus, the large community park, and the library. Very walkable. If we could have pre-selected what part of town we’d like to buy in, this would have been it. The neighborhood is, we hear, very cohesive, and there are retired professors (like me) right next door!
  • The ADU is a lovely little guest cottage with a bedroom, bath, small living space, a full kitchen, a little bistro set on the patio in front of it, and even its own separate entrance and street address. The current sellers have been making over $40K/year running it as an Airbnb. In our college town, places to stay, both short-term and long-term, can often be hard to find. They are also selling us all the furnishings for a very fair price.
  • The house has a gorgeous yard with redwood trees, a large covered patio, and beautful landscaping. The yard is probably our favorite feature of the home.
  • There’s an oversized secondary bedroom in the main house off the front door that we’re going to turn into the Peloton room/home gym. I’m very excited about that.
  • We’re going to get a dog as soon as we’re settled!
  • OK, now the “cons,” such as they are: The house is old. It’s a mid-century modern home built in 1965. I was very nervous about this, but our agent, who has general contractor skills himself, walked us point by point through the inspections and told us the place is in quite good shape. This style of house is very popular with many, especially in our town, but I’m used to a brand-new condo with all the work done. This is definitely a pivot, especially at our age (we’ll turn 66 this year). “Good shape” or not, it’s going to take more work and attention to maintain it. (I guess another pro is no more HOA. On the other hand, the HOA takes care of a lot of things.)
  • The kitchen and master bath are both cramped (that’s putting it politely), as things were back when the house was built. We’ve already met with a contractor and are going to have work done on the house within a month or two of moving in. So there will be that effort, expense, and disruption. (On the other hand–hey! We’ll have an ADU we can stay in or at least cook in while the work’s being done!)
  • Maybe the biggest con, or at least implication, is financial. We were living very comfortably in our condo with a manageable mortgage payment at 3% obtained in 2020. Even without our (high) HOA dues anymore, our housing costs will double. We also are using cash we’ve been sitting on since our previous move to the condo to come up with the down payment before selling our condo first. Once we get the money out of the condo, that can be used toward our remodeling plans. We’ve crunched the numbers and can afford the increased house payment, especially if we add possible income from the ADU. But we’ll have to watch our budget more closely than we do now. I’d be lying if I said I’m not a tiny bit anxious about this.

So it’s a “little” move (only a mile) but with big implications. Instead of drifting along comfortably in our condo, we’ll be moving, remodeling, getting a puppy, and possibly learning how to be Airbnb hosts. (We may also consider renting the cottage to longer-term tenants, but Airbnb allows us flexibility to use the space for our daughter if she needs it.)

I have lots of thoughts about what I’ve learned about buying, living in, and (hopefully) selling our condo, but I’ll save that for another day.

 

 

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Rachna Condos
18 days ago

Congratulations on this exciting new development. I’m sure it gives you peace of mind to know that (if needed), your daughter would have a place to call her own as she figures out her life. I don’t know if you looked into the option of a portion of your pension going to her when you pass away. It means less money now but the security of her having a stable income for her lifetime is huge. If she doesn’t need it thats the best-but if she does it will be a godsend and while we can’t control much when it comes to adult children, knowing that they will have a regular income without complexity can make us rest easier if we are concerned for their future.

Heidi - SunnyMoneyDIY
19 days ago

DrLefty – I so enjoyed this article and was living vicariously thru you. HOW EXCITING. One suggestion… Put the same amount of your old HOA fees aside in a ‘Future Renovations’ account for a couple years. I did the same with the money I used to spend on my old snow plow services when I moved south. I found it easier to give myself permission to spend it that way and every time I did pull something out of there it would tickle me all over again: “I NEVER HAVE TO PAY FOR TO BE PLOWED OUT EVER AGAIN!” Hahaha.

William Perry
20 days ago

Hi Dana,

Some thoughts after reading your post –

You may want to take a look at the tax rules regarding short term rentals. A potential trap exists if the average lease term for a property is seven days or less, then the taxing authority may consider your rental a trade or business activity. If determined to be a business the net income would be subject to self employment taxes as well as income tax.

Additionally, short term rentals with personal use can add a lot of record keeping work as the expenses have to be allocated between rental and personal. You may want to look at IRS Topic no. 415, Renting residential and vacation property.
If you ever sell this home the business depreciation, allowed or allowable, would likely be taxable and the gain on the sale would not be eligible for the exclusion under IRC 121.

I would also be concerned about other related rental issues from renting such as –

Does rental change how the property real estate tax rates are assessed?
Does the mortgage interest rate change due to the rental?
Does the rental impact your homeowners or other insurance?
Do you need additional or different insurance because of the rental?

I hope you have considered the possibility of having to live on the ground floor in the event future health issues precludes either you or your husband from walking up stairs.

Your focus on this move is on your daughter. If I were making this change I would consider that focus to be the primary guiding criteria in deciding how to use the ADU. Our adult children have all scattered across our country and I can think of nothing better than having any or all of them nearby and in the backyard in a separate unit would be near perfection to me.

One last thought, we have been in our house for almost 25 years and if I had the transaction to do over I wish we had put our home in a revocable living trust at purchase.

Congratulations on your new home. Best wishes for years of enjoyment.

Bill

Larry Sayler
17 days ago
Reply to  William Perry

Bill, is there anything that precludes you from putting your house in a revocable living trust now? I would not think so, but I am no expert.

William Perry
17 days ago
Reply to  Larry Sayler

There is not a legal reason. My issue in not doing so currently is there would now be the additional legal expense to re-title and record the deed transfer to the RLT (in addition to the legal cost to initially create the revocable living trust (RLT) which we do not currently have) and it is also my understanding that the particular, mostly unused, large home equity line of credit (HELOC) that we have would also have to be re-established and I worry that since I have stopped working and my earned income has ended I do not know if I would be able to get a new HELOC with the high limit and terms that my current HELOC loan has.

I expect that if my spouse dies first I would downsize my residence by moving and my wife would certainly have to move because of her current limited mobility should I die first. Thus when either of us dies or I become unable to maintain our current home a move is in our future.

Where Dana lives, in California, I believe she can choose to include a transfer on death provision as part of the titling in a deed in lieu of using a RVT but my state currently does not allow for TOD provisions in deeds. Fortunately my state intestacy provisions currently matches our bequest intents when including post death transfers via beneficiary designations and joint ownership. In the unlikely event that my wife and I die at the same time I expect the probate process is not so onerous in my state for what assets I will expect will be left as my state allows for a simplified administration process for small estates.

Last edited 16 days ago by William Perry
Catherine
20 days ago

I love this change for you!
I share my big old California house with one of my kids now since I’m mostly in my Arizona tin can casita.
I recently had the 95-year-old garage rebuilt, and refurbished the 1960’s era swimming pool. As my brother likes to say, maybe I’ll need to put the property on the market in 30 days or I might live in it another 30 years. Somewhere between those two points is my future. It was a project slog, but it’s done.. I also had financial jitters, they are also in the rear view mirror now. Whew!
Good luck with your move and projects.

Bob Smith
20 days ago

Dr. Lefty,
Enjoyed your article, I wish you and your wife well on your new venture.
As a couple who rented a detatched unit on our properties, I’ll add my 2 cents worth.
Vacation rentals, like AirBnB is a whole different story than a month to month tenant.
Think twice about hosting different people on your property several times a month, as opposed to a tenant signed on for several months, a contract outlining details.Hopefully over the course of that agreement a friendship is established.
I would think a college town would offer a fair number of tenants, being students or professors.
Nothing wrong with AirBnB hosting. We enjoyed it for 10 years in Hawaii. Where guests show up happy, with money, no boss, in our properties case no kids. Views to die for with the best air in the world.
But a different animal than long term renting
Requiring more book keeping, computer skills via AirBnB , meeting guests, comunication skills and of course cleaning. Above all cleaning. Of course all of which can be subbed out, at a cost.
I’ll leave you with, vacation guests have a different schdule than folks with jobs, living on your property.
Aloha

..

Edmund Marsh
20 days ago

Dana, the new place sounds perfect for you and your family. And you’ve avoided the pain of uprooting, for you and your friends! Now the search is over, what will you do with your extra free time?

Rick Connor
20 days ago

Congratulations Dana. Sounds like a great move. I’m very happy things have worked out so well.

Last edited 20 days ago by Rick Connor
Jeff Peck
20 days ago

Congratulations—what an exciting step. This sounds like a smart, thoughtful move for your retirement, your future flexibility, and your daughter. The walkable location, beautiful yard, private ADU, and space to truly enjoy life make it feel like much more than just another house.

It also makes sense to feel a little nervous. A bigger payment, an older home, and upcoming remodeling are real considerations. But it sounds like you did your homework, stayed within your means, and found a place that genuinely fits your goals.

Wishing you a smooth closing, an easy move, and a wonderful new season in a home that seems full of possibility.

Jeff

Michael1
20 days ago

Hooray! It sounds like a great get, despite the cons which you’re honest with yourself about. Awesome outcome.

Your comment about things moving fast reminds me of selling our last house. We went under contract within 24 hours of listing. Yours is a bigger deal, just makes me think of it.

Congratulations!

Michael1
20 days ago
Reply to  DrLefty

Keeps getting better 🙂

Mark Crothers
20 days ago

My, my… how exciting, congratulations to you both! My wife and I have been casually house-hunting ourselves, mostly in an attempt to escape our current half-acre yard. Casually, because it seems finding something suitable is far harder than it sounds — who knew that “less garden to maintain” would be such a niche requirement?

When we bought our current place years ago, we added a 2,000 square foot extension and did a major remodel, which involved knocking down most of the internal brick walls. I emerged from the experience a changed man, and not just emotionally. I can now tell you exactly what an RSJ (rolled steel joist) is, and why an acrow prop is your best friend when you’re removing a wall and would prefer the ceiling to remain where it is.
It’s quite the education. Enjoy every moment of
it!

Howard Schwartz
20 days ago

Best of luck with your new/old home. My wife and I sold our home of 32 years in September and moved 15 miles away to a 55+ community. I wish we had done it 10 years ago.

Dan Smith
20 days ago

Sounds like you guys are going into the new place with your eyes wide open, just don’t let the stress of the renovations burn you out. And I know a great obedience trainer for the new puppy; I wonder if Kristine does zoom classes.
This is a rare instance where I wish we could post pictures, as I’d love to see your new digs.

Kevin N
20 days ago

Congrats. I love the “very walkable” part. It’s great that you don’t have to depend on a car for everything. Sounds like a exciting new adventure!

Jeff Bond
20 days ago

Congrats, Dana! I look forward to hearing more stories as you settle into the new home. I know that having contractors in the house while you live there can be a challenge – so look forward to hearing about how it goes. Maybe I’ll write about that sometime, too.

Jack Hannam
20 days ago

We are in our early 70s, are retired and had lived in a two story home for 37 years. Good friends built a retirement villa in a nearby beautiful area, and suggested we buy the last remaining lot and build too. Zero entry home, top of the line appliances and all outdoor maintenance provided sounded very attractive. But we balked at the price.

We found a lovely well built 54 year old brick ranch style home for about half the cost, only a few miles away. No zero entry, but one level. I wasn’t so much concerned about discomfort from climbing stairs, but rather the fall risk. We moved into it six months ago. No HOA, but we hired trustworthy folks to handle all exterior maintenance. A good friend is a retired general contractor who gave it his seal of approval, and we check with him for advice on whom to call for any issues.

I think you and your husband, and your new dog will enjoy your new home. Congratulations!

Ken Cutler
20 days ago

Congratulations, Dana—this is an interesting development and based on what you’ve shared I think it will turn out to be a good move. We’ve had a successful multigenerational living arrangement for over eight years with our fully employed but not highly compensated adult daughter. Hopefully if you go that route with your daughter the new housing compound will be a great solution.

B Carr
20 days ago

Old? A small part of my youth was spent living in a house built in 1789.

Is your new place single story?

David Lancaster
20 days ago
Reply to  DrLefty

Remember though that a stair climb chair is always an option if you no longer feel safe climbing stairs. If you are wheelchair bound it is less of an option due to the need for two wheelchairs. The stair climber chair was perfect for my mother in law when she moved into our house at 102 yo as she was still walking with a walker and did so even up to her passing at 103.

mytimetotravel
20 days ago

Stopping by to say congratulations. Sounds like a great location. Best of luck with the alterations.

Michael1
20 days ago
Reply to  DrLefty

Definitely. I can’t think of a reason not to at least get in a list.

mytimetotravel
20 days ago
Reply to  DrLefty

Don’t know what the wait lists are like in California, but here you would be the perfect age to get on one. At most places there’s no need to accept an apartment when you get to the top of the list unless you’re ready, but do check for that.

mytimetotravel
19 days ago
Reply to  DrLefty

Congratulations on selling the condo!!

It seems to be common here for entry fees to be 0, 50, or 90% refundable, with a corresponding increase in the cost. I opted for 0%, as I am not overly concerned about leaving a legacy. There is a for-profit chain that uses a condo system.

My CCRC seems to be the preferred destination for retired faculty from one of the local universities. Other area universities have different preferences. You might check to see what your former colleagues are doing – depending on how you feel about them it could be a plus or a minus.

Marilyn Lavin
20 days ago

Sounds great!! I’m glad you’re prioritizing getting the puppy. It’ll assure you get to know your neighbors very quickly.

We’ve never lived in a place with an HOA, and our house was built in 1917. My husband has a good contractor on his speed dial, so not a problem. We also use a service for snow removal (not a problem for you) and yard maintenance. I don’t think our costs are greater than HOA dues and we control what and how things get done.

ADUs seem to be getting increasingly popular—we have neighbors with a setup much like you describe. I suspect it has added a lot of value to their property.

Congratulations!

baldscreen
20 days ago

Dana, I was really happy to read about this new adventure of yours. It sounds like a lot of work, but will be worth it in the end, though. Looking forward to reading about your ups and downs as things progress. Chris

kristinehayes2014
20 days ago

How exciting!

  • My favorite line (no surprise): “We’re going to get a dog as soon as we’re settled!”

I will, of course, need to know all the details. And we do offer training courses near Phoenix :-).

David Lancaster
21 days ago

Hi Dana,

Great to be “hearing” from you again.

I’m curious about your experience with the new changes post the class action settlement with National Association of Realtors with the seller no longer needing to pay both agents. I hope you could write a brief post about this after you have sold your condo so you can address the experience from both the buyer and seller side.

R Quinn
21 days ago

Perspective is interesting. The house is old- built in 1965. Our first house was built in 1918 and our second in 1929. They are both still standing 😎

Linda Grady
21 days ago

Congratulations, Dana! It sounds wonderful and now that you aren’t preparing for classes, I’m sure you’ll find that the home improvement and maintenance projects will keep you busy, in a good way, during these first few transitional years of retirement, not to mention the care and training of a new dog 😉. My very best wishes. I’m looking forward to hearing about the inevitable new adventures.

Jo Bo
21 days ago

Dana, thanks for the update. This new move seems to position you well for increased social connection — the neighbors, the vibrant community, the Airbnb, even the new puppy. In that sense, it seems like a smart move. It would seem responsible too, by being affordable, walkable, and potentially helpful to your daughter. Maybe even by being a dwelling in which you can successfully age in place? Your writing conveys much enthusiasm for the purchase even considering the cons. My hope is for you to enjoy your new home and associated projects, and to think of them as fruits of your saving and career.

Nancy Moser
21 days ago

Dr.Lefty, first time commentor here on HD. Please keep contributing posts. I have really appreciated your articles on your parents and children. I truly hope you and your husband will enjoy your new home and never regret your decision. I look forward to reading more of your posts in the future.
Nancy

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