>>719704872
Before reaching Benny, figuring out the beginnings of what build you want to do this time around and what weapons you can find along the way that complement it (and what skills complement the obtaining of said weapons, like a 75 Lock leading to the unique Lucky revolver). After reaching Benny, the myriad of combinations you can use to lead with the different factions for the endgame battle: each of the Strip families, the Boomers, the Khans, etc.
Being Mr. Perfect and becoming friends with all of 'em is fun for a couple playthroughs, then you start experimenting and fucking around with ones or sabotaging others. New Vegas' greatest strength is how often it reacts to player choice, be it in skill dialogue or quest consequences.