Suzuki GS500, or a Kawasaki EX500. both very cheap, reliable as a hammer and easy to ride. no plastic parts to break when you drop it. (and you will) and they've not changed in years, so prices are low. aftermarket parts are plenty available (if you like to tinker)
IMHO, a 250 is fine for around town, but you'll be hard pressed if you've got any highway riding to do.
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