Realistically: a new bonneville or scrambler after I'm out of college.
If I won the lotto: K0 750, Duc 750 or 900ss, rc166, cb92r, cbx, cx650t, suzuki re5, any knucklehead, an early sportster, black 850 commando, a flying merkel (because the name is so cool), ......... and on and on until I basically fill a warehouse and have my own personal museum.