If you are going to keep your 250 once you get your full licence then you should ignore the price, and just buy the best bike you can. But most riders upgrade to a larger capacity bike once they legally can. So if you are planning on moving to a larger bike, get something cheap - you will still lose money when you sell it, but losing 40% of a $3000 bike is much much better than 40% of a $10,000 bike.
Looking new, there are only a couple of choices in the $3000-3500 range, both chinese, ie the GN250 cruiser and the Lifan 200 trail bike. Neither is particularly exciting, but both go well enough for learning on, and with a new bike you have the advantage of warranty. And buying new, you know the price is right - you arent paying more than the market will support !
The GN is a better bet if you have no interest in off road riding - its modestly more powerful, and goes better on road. The LF200 is great if you want to go down the beach or try an adventure ride, but it has a narrow seat, and will be close to its max speed on the highway.
For commuting, the LF200 is BETTER than the GN - I mean it ! Its got better brakes, its higher so you get better vision, and trail bikes actually get more "cred" with car drivers, most likely due to the extra height.
David must play fair with the other kids, even the idiots.
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