r/AdvancedTaxStrategies

A few months ago I started selling in a fourth state and realized I now had four different due dates, four different rates, and four sets of filing rules to track by hand every month. Last week I almost missed a deadline because I was heads-down on a product launch, and that near-miss made me wonder if I've finally hit the point where doing this myself is riskier than handing it off. Is crossing into multiple states with overlapping deadlines the real signal, or is there something else that usually tips people over?

I have about a $1M tax bill coming up in 2027 from capital gains realized this year. The sale has already happened and I live in Texas.

I’m already looking at tax-loss harvesting and possibly buying/operating another short-term rental with cost segregation/bonus depreciation (btw spouse qualifies for rep status and has several LLCs that have losses). What other legitimate advanced tax strategies should I be looking at before year-end?

How do you track your contributions and penalty free withdrawals before age 60?