@RB: I have not quoted parts of your reply. I agree with, or at least understand, the parts that I have left out.
Those things don't make any sense if the OP can convert with 0 taxes, so why bring them up for consideration? That's my point. If you think it's useful to give considerations that clearly don't give them any benefit is worthwhile, we'll just disagree.
Well, as the Spartans famously said, "If."
Yes, if the OP can convert with zero taxes, then the considerations I listed may be moot.
I think the situations where actually doing so are quite limited, so I hope the OP will reconsider the premise.
If they do and decide that converting with zero taxes isn't actually possible for them, then the considerations I listed might then become important.
I guess I'm fairly confident that OP will figure out that it's not actually zero tax impact for them.
And even if it does turn out to be zero tax impact for OP, there are other people who are reading this thread for which my comments may be relevant. I write for the world, my friend.
Similarly, if one has major medical expenses later in life and no IRA, they could sell some of those appreciated funds and the income from that could be used to write off the medical expenses.
Emphasis added. I still don't fully understand.
Selling appreciated funds does create income.
One can deduct medical expenses beyond 7.5% of AGI, and also subject to the usual limitation that itemization would need to make sense.
But selling appreciated funds is also generally going to increase AGI. This is generally going to increase the 7.5% of AGI limitation and is generally going to reduce the amount of the medical expense deduction.
If you mean that you're going to use the proceeds from the sales of the appreciated funds to pay the medical expenses, then sure, that makes sense.