So I'll respond as the ultra conservative financial guy. Before retiring, I saved about $350k in cash. I was worried about having the cash available. As I retired, I started doing the math on Medicare IRMAA, future RMDs and social security. Our majority of savings are in traditional IRA accounts which is bad because of two things. One, as I take money from them, I pay regular income tax. Second, at RMD time, I have to take money out. Regardless, these two things add to IRS labeled income, or MAGI if you want to get technical. You're probably thinking "who cares?". Well, not only do these push us up brackets but if you've saved too much like we have, they, alone are enough to push us over the IRMAA Medicare penalty limit.
So, of course we are doing Roth conversions now. Oh, and don't forget that in 2026, the tax rates go up again. So what are we doing with all this "income" pushing us towards higher taxes and IRMAA penalties?
1) converting cash to taxable account, buying BRK/b because it doesn't pay dividends.
2) Roth converting up to where income is just under IRMAA (I'm on Medicare now, so if you're not, that limit does not exist)
3) In taxable accounts, sell all dividend producing ETFs like VTI and SCHB and convert them to BRK/b. In tax advantaged, dividends don't matter
4) and this is important: Make a spread sheet to keep track of ALL income. I really don't want to go $1 over the IRMAA limit and spend an extra $100 a month on Medicare.
5) If you sell tradelines, you're getting a 1099. Don't forget this. Keep track as this is income.