I'll throw my $.02 in...
Haven't seen anyone mention Quicken. 20 years ago I started logging EVERY penny I spent into the software program. I had always kept a balanced checkbook, but that didn't explain where all the money went. Now I know, and it's helped me be aware of how to control spending. Found out I was spending more on bridge tolls than wine!
I buy new cars and keep them until they die. (No hidden problems like in used cars). Once I paid off the first loan, I kept making payments to myself in a separate account for the next car which I paid cash for, and same thing for the third. So I've had no car loan since 2002.
For a retirement plan, ALPA pays Schwab to do one for us for free. Very detailed product, and if you've paid yourself first over the years, will give you a warm fuzzy.
Gotta step...enjoy talking money with like minded pilots!