To Roth Convert or Not

I’ve been doing a lot of reading on Roth conversions lately, and I’m seriously considering pulling the trigger on one this year. But before I make any moves, I wanted to get some feedback from those of you who have been through the process.

A little background: I’m in my mid-50s, still working, and in a relatively high tax bracket. I have a mix of retirement accounts – mostly in a traditional IRA and a 401(k). I also have some cash on hand to cover the tax hit if I go through with the conversion. My thinking is that tax rates could go up in the future, and I like the idea of locking in my tax bill now instead of worrying about it in retirement.

I’m looking for a financial advisor to help with this. I found one near me that people praised on reddit. They seem to cover mega backdoor roth conversions but I wanted to get some other points of reference first. I’ve also read this article on Roth conversions but I had some additional questions I’ve been mulling over:

1. Tax Implications: I know that converting will bump up my taxable income for the year, which could push me into a higher bracket. Has anyone found a sweet spot for how much to convert each year to minimize the impact?
2. Medicare IRMAA Surcharges: I’ve read that a higher taxable income could trigger higher Medicare premiums later. Has anyone run into this issue?
3. Breaking Even on Taxes: If I pay taxes upfront, I need to make sure my Roth account has enough time to grow tax-free to justify the conversion. Is there a general rule of thumb for how long it takes to break even?
4. Market Timing: Does it make sense to do a conversion during a market downturn? I feel like paying taxes on a lower balance could be beneficial if the market rebounds later.
5. State Taxes: I live in California so I’m wondering if I should factor that into my decision-making.

I’d love to hear from folks who’ve done a Roth conversion – either all at once or in stages over time. Was it worth it in hindsight? Anything you wish you had done differently?