I'm moving to more vintage because it's less volatile, you really don't have to do any prospecting on who's going to make it and who's a bust. Rarely do you see big drops in values, or see players like Braun or Arod get in trouble and then you can't give their stuff away. The vintage players...
My suggestion on vintage is not get too worried about condition at the start. Buy what you can afford and of players you like. There's lots of decent condition star cards out there that can be found at good bargains. I look for decently centered stuff, allow for less than perfect corners but...