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Jiggles - I appreciate the response seeing as you have a 650. Plenty of good reasons to keep the 250 but sometime within the next year I will trade to something that fits my riding interests a bit better. At most I'll put 5000 miles on it this year and trade up next year. Just a matter of how long I should wait. I may end up on a tourer like you suggested but I prefer the look of a sport bike and would likely look for a sport bike that can be a good sport tourer.
Thanks for you advice on the tires. I will probably just get new ones. Rosso II and BT seem to be concensus 1 and 2 on this board so I'll go with one of those for how ever long I rock my 250.