After two years (first 2 yrs of retirement) of paying penalties for my taxes I'm actually owed money on my federal return. Haven't done the state but I'd imagine the same to be true. I find taxes to make no sense in many situations and the tedious nature of them causes me to hate looking at that stuff. Two years ago I got hit with a big penalty in my first year of retirement because I overlooked how much interest you can make on holding house money in accounts. Last year I would have been ok but after doing a Roth conversion I was going to pay taxes out of another account and forgot about it.

This year I started off with early payments and tried to track things more closely. Next year if our income is about the same I might just pay the safe harbor amount to avoid any surprises.

This is also the first year I decided to do them myself with FreeTaxUSA. Prior to 2025 I had to do taxes in multiple states and had a CPA that would do it for me at a very reasonable rate. The only thing I have to double check is whether I have any carryover losses from last year (I doubt it).

Although I've always known it but it is definitely important to consider long term investments to avoid short term gains (unless you are into some kind of day trading, etc.).

Either this year or by the end of 2027 I will finish off my inherited father's IRA. Well before the 10 yrs but I wanted that done before social security starts to avoid any issues with taxes.

Rich