Recently, I've been experimenting with a small little tool that allows you to set up some character challenges in New Vegas: Scenario Generator.
It's easy to use: Just go to the website, and then choose Fallout: New Vegas. For F:NV in particular, what the website does is it generates a new character set-up, i.e. S.P.E.C.I.A.L., Tag Skills, etc. However, it also dictates the companions you take along with you, how much you engage in unprovoked murder and theft and, in the end, the ending you'll get.
It's quite marvelous, yeah, but let's talk about my current story:
My character was generated with some pretty sweet S.P.E.C.I.A.L. stats...except in Perception, which was unfortunately a measly two. Not only that, but two disasters happened: 1. I didn't get the amazing Wild Wasteland option (you can only reroll columns if there's any contradictions, or it's just impossible to play with), and 2. I was required to use Energy Rifles as a primary weapon, with the appropriate tag skill with it. The only problem? Perception also determines Energy Weapons, so...it was pretty low, even with the tag.
So I went through the game, occasionally murdering people (Trudy and Oliver, that guy who won the lottery), and stealing some stuff occasionally as well (e.g. ammo). I'm as far as Nipton as of right now, but I'll update as time goes by, with different posts.
But do try Scenario Generator, it's an excellent tool and I recommend using it if you feel like replaying F:NV.
It's here if you want to check it out.