I am 62 and mostly retired. I am also on Obamacare until Medicare kicks in. I live mostly off withdrawals from my assets. I have a mixture of appreciated and non-appreciated securities outside retirement plans and both traditional and Roth retirement plans. My accumulated unrealized capital gains are relatively modest and I have no heirs to plan to leave assets on a stepped-up basis. I am of course eligible for Social Security and also for a modest pension. My earned income and taxable dividends are maybe $20K a year, and for tax purposes I can reduce that by contributions to my IRA and Keogh.
While I consider myself extremely facile in both taxes and financial planning for someone with no actual credential in either, I go on overload trying to create a sensible multi-year plan. Between the sliding scale of Obamacare subsidies, extra Medicare Part B premium, tax on social security benefits when I take them, etc., my head spins. Prior to last year I was on COBRA from my ex-wife, and I would simply realize capital gains or do Roth conversions to hit the top of the 15% bracket (0% for capital gains) and felt what I was doing was sensible. Now I'm not sure. This year, my first full year on Obamacare, I'm trying to keep my reportable income very low. My retirement funds are maybe 60% Roth, 40% traditional.
My question is, is anyone aware of a tool that will let me optimize my income streams over time? In theory I'd like to say "Here are my assets, assume X% growth per year, here are my options for social security and pension, I need $Y per year growing with inflation, tell me the schedule of where I should go for money each year to minimize my overall taxes."