If I won the lottery (i.e. I had "stupid" money to spend on guns), I'm not sure how different things would look than now. Sure, I'd probably pick the S&W or Colt instead of the Taurus when shopping revolvers (with the 865 Defender and 905 Defender as exceptions since S&W and Colt don't really have something quite the same). I'd probably take the Colt Gold Cup Match out of consignment that I took the to dealer when I decided I liked my Dan Wesson Heritage more (on a teacher's salary, I can really only afford one "expensive", i.e. over $1000, 1911, and the Colt went for consignment when I decided I liked the DW more). I'd definitely finally replace the S&W M57 I never should have sold. I might pick up things I want to try a little quicker. However, I'm moving towards trying to cut back, not necessarily on numbers, but on totally different styles, so my limited range time could be more productive and I will be better with what I have. That said, I'd likely buy thousands of dollars more in ammo (for each caliber I have), and join one or two more ranges (I can only really afford to have one membership, and if they are busy, they are busy... "stupid" money would let me join a few so if one if too busy, another might not be).
I'd also probably buy a professional style simulation suite and laser pistols and convert a room of my house.