I'm on my first play through, and I'm around as far as confronting Benny. I'm playing a non-combat oriented build, so I already have most of the weapons I'll be using for the rest of the game (all the good stuff can be found instead of bought, anyway). I'm also sticking to light armor because it helps with sneaking and I'm about to start using a mod that puts weights on everything so I want to travel as light as possible. As of now, I have reinforced leather, which is probably the best until my survival is high enough for the gecko armors. Lastly, I have every implant I plan to get. On top of this, I have $20k+ caps (not including NCR and Legion cash). I haven't even played in a casino yet (why bother, right?).

What I'm thinking of doing is starting over, with the weight mod, and not allowing myself to use any storage whatsoever (so no home). At least it would make it difficult to get so rich so fast. Anyway, is there ever going to be a use for all this cash?