I would be Hugh Hefner "THE VIDEO GAME CHARACTER" in the video game you play as Hugh Hefner in your mid 20's so believe me I've got plenty of life left.
Probably a fisherman. You know the ones that stand on the deck, in one place throughout their entire lives and might occasionally ring the main character up to tell about their awesome Magikarp? Them buggers...
But instead of fishing pokemon, I'd instead have something like a Syther, Jolteon and Vulpix... just to confuse my battler.
All my crappy fishing pokemon would be on Bills computer, of course.
Maybe Shirou Emiya from Fate/Stay Night as well. Just because he gets to bone Sakura, Saber, Rin and Rider ^_^. He also has a hot sister-like-figure (who isn't his sister ). Sure, he's a complete weakling who comes too close to death numerous times (Gets his whole arm cut off, gets his chest blown up, gets pierced in the heart by a lance etc). But with his harem on his back, he's always gonna survive .
Besides, he doesn't stay dead when he dies. When you make the wrong choice in F/S:N and come to an unfortunate end, you get a funny cut scene which gives advice on what you should do instead and then you load your last save
Shirou goes through fifteen days of hell and then lives his life as a guy who somehow gets all the girls.