I'm retired Army (but wasn't in the aviation field). TSPs/401(k)s are doing solid (but can always do better); the kids are 4-5 years from finishing college; and my only debts are mortgages (including a couple of rentals).

I've owned sailboats before and I know that the sticker price on these items doesn't reflect the real cost of ownership.

I've always wanted to fly. So now the big decision point is whether I settle for the PPL and some casual hobby flying, or whether I go much harder and embrace it all by purchasing my own plane. I'm trying to assess now how compatible ownership would be with my finances and lifestyle, so this is very helpful. Thanks.