Can I do tIRA to ROTH conversion and tIRA + HSA contributions at the same time?

[tenant13]

I'm turning 55 and ready to retire. I have a regular savings account that I'm planning to use as my main source of income for a while - withdrawals would be tax free, the interest it generates: say $3k would be taxed as my ordinary income. So would be the conversion. I'd like to convert 19,95k a year. But I would also like to contribute max allowable amounts to both tIRA & HSA (by transferring money from the savings account). If I add up standard deduction (12k) + tIRA deduction (6.5k) + HSA deduction (4.45k) my total deductions would be 22,95k which would knock my taxable income to 0. Hence no taxes paid. Does that make sense?

The thing I'm confused about is selling equities and the LTCG. Could I sell equities from my regular brokerage account and still pay zero taxes with the above scenario?. And how much could I sell? Full 38,6k? Or 38,6-22,95?

[maizefolk]

If you don't have any earned income (depends on your own personal definition of retired) you won't be able to make a tIRA contribution or take the deduction.

[MDM]

maizeman already covered the apparent no-go on IRA contributions.

But there is no "earned income" requirement for HSA contributions.

And you might be better off converting traditional account money to Roth while paying very low tax rates.  See the '0% LTCG or t->R' tab in the case study spreadsheet.

[tenant13]

Thank you for clarifying it and the link to the case study. I still have time to educate myself :)