would you consider a suzuki sv650? a bit bigger but if you don't get too aggressive to quickly it'll reward you in the end. the 250 is a great little commuter, but if you're anything like me, you'll likely want a bit more power after the first few weeks.
another consideration...naked bikes are usually far less expensive.
Not sure if you'd consider harley, but the 883 sporster's can be had relatively cheap and ladies love harleys
most guys on here will tell you HD is crap, junk, tractors, blah blah blah. sporties are actually a LOT of fun to ride, the stock tires are composed for mileage more than grip and get about 60mpg. dirt cheap insurance too.
