Best jobs: Chief Financial Officer of any corporation you could name, past or present (q.v. my skill at Capitalism II, the Patrician/Port Royale series, and Koei's Aerobiz games), city planner (SimCity and every game in its genre), or generic magic-user type (Morrowind/Oblivion). Defensive player on a football team (Madden/NCAA Football).
Worst jobs: Anything requiring stealth (Metal Gear Solid series), driving around shooting/killing people (Grand Theft Auto, the entire FPS genre), or cooperating with other real live humans (the entire MMORPG genre and multiplayer in general). Games I suck at are noted.