If you generate nearly all of the income in the last quarter of the year, you may be able to pay your tax in January without a penalty but you'll really need to know what you're doing with Form 2210. The safest way to pay your taxes is through withholding but that's not always practical; equal payments throughout the year using safe harbor amounts is safer but you are paying "early"; if you do try to bunch everything in the fourth quarter, I'd definitely recommend speaking with your CPA about the tax ramifications and Form 2210 since it's a very intimidating form (but it can be workable).
You're facing a dilemma that many will face. If you want to buy a place before selling your old place, it's all going to come down to cash flow. In your case, (1) you don't have the funds in a taxable account to purchase the new house outright; (2) you don't have the funds in a taxable account for an SBLOC; (3) you probably won't be able to get enough from a HELOC although you didn't mention specific amounts; (4) you probably won't qualify for a bridge loan if you're retired without work income although you should look into it; (5) you can't replace the money in the Roth unless it's very short-term and you mentioned it might "take a while" to sell your current place. Given all of that, you'd probably be better off renting in the new area, selling your current home, and then using the proceeds to buy another home. I don't see how your cash flow is sufficient otherwise based on what you've described.
There are many benefits to a DAF and one of them is time. I've used our DAF for many years to donate appreciated assets as a rebalancing tool. During prolonged and significant equity appreciation, it's a great way to bring your equity risk back down to manageable levels. But once you have the assets in the DAF, you can use it as a family project to decide what charities you may want to support for the year (or longer). It's an opportunity to teach your kids about the importance of philanthropy and gives you time to research charities properly.
A lot of good people out there! However, it really does have to be Jonathan Clements. It's not just about the money itself. It's about what it signifies and the place it has in maneuvering through a tricky life. It's great to be able to discuss asset allocation, staying the course, and low cost index funds, but it's how you use the money that ultimately matters in the end. Jonathan has taught me that year after year, and just gets more meaningful over time.
A lot of terrific information here, but one thing I'd really stress is understanding what exactly your state allows regarding switching supplemental plans without underwriting. Some states are extremely generous (such as no restrictions with switching); some states allow some flexibility (such as allowing a subscriber to go from a plan with a lot of benefits to a plan with less benefits); and, some states are very restrictive and allow very little room to maneuver changes without underwriting.
QCDs are a great way to give! One small word of caution: when you're using QCDs, you're responsible for making sure that everything's documented properly. Meaning, you'll still need a letter from the charity stating you've received nothing in return for your donation (just like you would if making any donation and deducting it), and you're responsible for making sure the check is cashed. You don't want to find yourself in a pickle if that check you sent in November somehow gets lost. For this reason, QCDs early in the year might be a good option overall.
Comments
If you generate nearly all of the income in the last quarter of the year, you may be able to pay your tax in January without a penalty but you'll really need to know what you're doing with Form 2210. The safest way to pay your taxes is through withholding but that's not always practical; equal payments throughout the year using safe harbor amounts is safer but you are paying "early"; if you do try to bunch everything in the fourth quarter, I'd definitely recommend speaking with your CPA about the tax ramifications and Form 2210 since it's a very intimidating form (but it can be workable).
Post: Don’t Let a Roth Conversion Trigger a Penalty
Link to comment from July 11, 2026
You're facing a dilemma that many will face. If you want to buy a place before selling your old place, it's all going to come down to cash flow. In your case, (1) you don't have the funds in a taxable account to purchase the new house outright; (2) you don't have the funds in a taxable account for an SBLOC; (3) you probably won't be able to get enough from a HELOC although you didn't mention specific amounts; (4) you probably won't qualify for a bridge loan if you're retired without work income although you should look into it; (5) you can't replace the money in the Roth unless it's very short-term and you mentioned it might "take a while" to sell your current place. Given all of that, you'd probably be better off renting in the new area, selling your current home, and then using the proceeds to buy another home. I don't see how your cash flow is sufficient otherwise based on what you've described.
Post: Thinking of a possible reason to tap Roth earlier then planned
Link to comment from July 11, 2026
There are many benefits to a DAF and one of them is time. I've used our DAF for many years to donate appreciated assets as a rebalancing tool. During prolonged and significant equity appreciation, it's a great way to bring your equity risk back down to manageable levels. But once you have the assets in the DAF, you can use it as a family project to decide what charities you may want to support for the year (or longer). It's an opportunity to teach your kids about the importance of philanthropy and gives you time to research charities properly.
Post: Why I use a Donor-Advised Fund
Link to comment from April 11, 2026
A lot of good people out there! However, it really does have to be Jonathan Clements. It's not just about the money itself. It's about what it signifies and the place it has in maneuvering through a tricky life. It's great to be able to discuss asset allocation, staying the course, and low cost index funds, but it's how you use the money that ultimately matters in the end. Jonathan has taught me that year after year, and just gets more meaningful over time.
Post: Something About Harry
Link to comment from October 19, 2024
A lot of terrific information here, but one thing I'd really stress is understanding what exactly your state allows regarding switching supplemental plans without underwriting. Some states are extremely generous (such as no restrictions with switching); some states allow some flexibility (such as allowing a subscriber to go from a plan with a lot of benefits to a plan with less benefits); and, some states are very restrictive and allow very little room to maneuver changes without underwriting.
Post: Medigap pricing question
Link to comment from October 15, 2024
Wonderful interview in every way.
Post: The Long View Podcast: Jonathan Clements: ‘Life Is Full of Small Pleasures’
Link to comment from October 15, 2024
QCDs are a great way to give! One small word of caution: when you're using QCDs, you're responsible for making sure that everything's documented properly. Meaning, you'll still need a letter from the charity stating you've received nothing in return for your donation (just like you would if making any donation and deducting it), and you're responsible for making sure the check is cashed. You don't want to find yourself in a pickle if that check you sent in November somehow gets lost. For this reason, QCDs early in the year might be a good option overall.
Post: Our annual give it away meeting
Link to comment from October 15, 2024