Originally Posted by ShardPhoenix
One I can afford!
In all seriousness, I'm not trying to be super picky since I've only got $2,000 to spend and I'm buying used. I'd like to find a cruiser in the 250-750cc range. I will say I'm kind of fond of the Suzuki Savage/S40's because I like thumpers. I'm also keeping my eyes peeled for Honda Shadows and Yamaha Viragos. Year doesn't matter too much, but condition is important. I'm not allergic to doing maintenance, but I don't want a big project.
I don't need something uber-powerful or whatever, as I'm not one of those "bigger is better" types. I know full well that a Honda Rebel 250 (or something similar) would suit my needs just fine.
Of the bikes you mentioned I say go with the S40. You will not be happy with a 250cc cruiser for long. It is not a case of bigger is better... It is more a case of what the bike is capable of doing.
Also have a look at a Ninja 250. It is likely the only 250cc bike that falls in your budget parameters that is capable of sustained highway speeds. They wrap it like a Sport Bike but it is a Standard
The little Ninja will make you laugh out loud where the others will only garner a smile.