im 35, just traded in my 2009 suzuki M50 for a 2011 cbr600rr. no comparison, of course. if you get a cruiser, you need a BIG one since 2 cylinder v-twin engines are a classic case of apples and oranges. just dont have the power for passing on the highway and getting you up hills and such unless youre well beyond the liter mark. the suzuki M90 would be a good start, my M50 was too small. the stryker or whatever that things called is also pretty awesome.
todays cruisers are more sporty, can lean them over farther, and that sort of thing but you really need at least a 1200-1300. i consider a big cruiser engine an absolute must if youre gonna have a passenger.
get an airhawk for your seat.