It’s great that you’ve got a good dealer in your area. I’ve seen good and bad. But keep in mind that even the most well intentioned dealer is still there to sell you a bike — it may be the best one on his lot for you, but it’s still most likely focused on what he has in stock or can get his hands on.
One bit of advice: Don’t be rushed. Sit on lots of bikes — including a couple that may not be in your immediate sights (dual sports, a cruisers or two, maybe even something with 600ccs). Sitting on one will give you some perspective on how the 250 really fits.
Also, I’ve had great experience with used bike and would not be afraid of them. A bike that’s just a few years old can be just as reliable as a new one and there’s no issue getting parts/service for something that’s been built in the last 10+ years (I ride a ’94). As long as it hasn’t been crashed — and that’s usually pretty apparent — a used bike can be a real bargain and you can often sell a year or two later for close to what you paid.