If you insist on a cruiser...
For that kind of money I'd look for a used V-star 650 or Shadow 750, or a Virago 535 for a little less -- all have more room to grow, not to mention shaft drive for lower maintenance. If you prefer the 250s then I'd still go used, as the Rebel and V-star 250 (previously named Virago 250) have been made since the late '80s and are all over CL for under two grand asking. But...
If you can be a little more open-minded (remember WHY you just went to the dealership?) you owe it to your family to consider a dual sport like a DR250/350, TTR225, CRF230, KLX/KLR. Something also capable of going off road, where you can learn priceless low-traction bike handling skills at lower speeds and practice/play away from traffic.* It won't cost any more than a small cruiser, is arguably more practical (designed for abuse, thus often cheaper to drop), and might be a little less selfish (if I'm not reading too much into your post).
Take the MSF. I think they may even have loaner helmets, in which case, take the MSF *now*. :)
There are a ton of helmet reviews on webbikeworld.com. They are suspiciously light on negative reviews but make an honest effort to quantify noise and ventilation.
Buy a proper full face helmet. Look at Gary's ugly mug and imagine how much worse that would've been if he'd been wearing an open face or modular. ;) (Sorry, Gary.)
DOT = legal for road use
Snell = crash tested/certified domestically
ECE = crash tested/certified in Europe
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*This is some advice I really REALLY wish I had received when I first started riding.