S40 Heard nothing but good about these bikes. And because i've been going bike nuts lately, i've seriously considered swapping out my katana for one.
Virago Heard lots of good about these too. small, good on gas, looks decent, $$$
V-Star
LTD
Rebel Small, (might be too small, have a seat on one and let your butt and knees decide. actually that goes for all of these) been around a good long while, cheap insurance, cheap price, leaves you leeway to get gear too. good good resale price when/if you decide you want something meatier on the 250's
nighthawk same story as the rebel i would say, not exactly a cruiser. but its got 2 wheels. thats enough for me.
VLX with 5k to spend you are going to be gear poor.
Then of course there are the hyosung bikes. some people are nervous about em, id snatch one up in a heartbeat. And there is a review floating around somewhere that has the virago, rebel, gz250, and the hyosung cruiser all being reviewed by newer riders.