In the 250 cruisers race, you might consider the Yamaha V-Star 250. They look a lot better than the Rebels.
Yes I owned one of those myself.
I rode it around for a while, and just decided I'd rather have a car.
250's are not as easy to sell as you might think (around here at least). I thought I got it for a sweet deal, it was below book. It was a 2008 in 2010 with I am thinking about 4k miles. I paid $2100 for it. I ended up selling it for that exact same price (and felt LUCKY to get it). I think the book value was up around $2500. It took me about 4 months to sell it, I first listed it at $2400, and not so much as an inquiry, I dropped it down to $2100 and it sold. I have seen similar bikes on craigslist... and still there a year later. Maybe the market for motorcycles is pretty bleak in general, so it might not be limited to the 250s.