My food for thought on the 250 is first that it gets 80mpg. I know I won't get that but I'll be taking back roads to work everyday and this will be my commuter. I'll keep it even if I upgrade later. For the fuel economy, price and my experience level, it seems like the best option right now.
Yep. Been there. Still there. The 250 is one of my two bikes and I was getting 74mpg city.
I agree with most here in that I recommend that you to explore the used 250's available in your area before you make the purchase. You can usually get a close-to-spotless bike with less than 3,000 miles on it for $1500 or less if you watch and wait. I don't know what your area's like, but there's a pretty clean '07 with a couple of extras in the Pittsburgh CL right now @ an asking price of $1400 with 7,000 miles on the clock. When the first flakes of snow fly here, the prices being asked usually plummet.
You can take a very small part of the $2300 you save and pimp the thing to your heart's desire like I did to mine.
I'm much happier with it than I ever would have been with a brand new stock purchase.
As far as the dealers, I was offered a new 2012 in the summer of 2012 for $3750 OTD. That included tax, title, plates, everything.
Even with the Yammi MSRP increase in 2013, I wouldn't even think about paying $3800 OTD for a year-old model.
Just a thought, if I'd only had one bike, I'd have missed the last 5 weeks of riding. A lady on script narcotics rear-ended me on my 250 and her insurance company has tried to screw me as many ways as they possibly could. Had I known they were going to be this way, I would have demanded a rental just for the sake of justice. I would have also missed any decent riding opportunities for the next month or two while I wait for the state to send my certificate of salvage, then repair the bike myself (essentially providing my own labor for free), and then jump through the hoops of getting it back on the road with an "R" title.
'03 650 Custom and '95 Cherry 250 Virago:
Kuryakyn Flame Grips. Chrome Covers.
Bullets w' 6.5W 350LM LED Bulbs.
Relocated Rear Signals.
Padded Sissy Bars and Luggage Racks
Lowered. Jardine Rumblers.
Re-Jetted. Corbin Stinger Seat.
Mustang Tank Strap. Large Inspire Bags.
Yamaha OEM Windshield. Purple LEDs.
Chrome Tank and Fender Trim. Eagle Embossed Fork Bag.
Classic Windshield. Mutazu LN Hard Bags w' Lights.