Good topic. I think there were not only guys who would of done well from yester-year but, might of even flourished. The Dynamite Kid was at least 15 years ahead of the game in terms of wrestling ability & cruiserweight style of wrestling. Roddy Piper, Jake Roberts, Mr. Perfect & Rick Rude were all human heat machines and I think Mr. Perfect especially with his gimmick would of been world championship calibur nowadays. And could you imagine Million Dollar Man & IRS coming out and gloating about their wealth while running down everybody else being effected by the recession? GOLD GOLD GOLD. lol.
However, for guys like that there would also be guys that would of never had nearly as much job security nowadays as they did back in the day. Junkyard Dog, Butch Reed, George Steele, The Bushwackers, Brutus Beefcake, The Killer Bees, Adrian Adonis with his drag queen gimmick all come to mind. These guys had YEARS worth of tenure in the WWE where in modern days they'd be lower card jobbers and released within 90 days of being brought up from FCW.