Join Date: Mar 2011
Location: Ottawa, Canada 2001 ZX6R
OP, if you don't plan on keeping the Ninja300 for at least 2yrs, then scrap the new appealing look and go for one of the '08+ Ninja250. You're better off spending an extra 500 into gear than the newest bike.
Why do you wanna take the depreciation for buying a new vehicle? Ninja 250s resell for the 90% of price you bought it for (if not dropped in between).
For areas with winter break (too cold) the best time to buy is now or until end of February.
Bikes are tough (especially Kawi, Gixxer and older CBRs) so I wouldn't be too worried buying anything used that doesn't look broken on the first impression. Even if it didn't get regular oil changes or chain care, worn bearings, etc. They keep going and with some TLC forget about the previous bad care.
I really wouldn't go for a brand new as 1st bike. If you still want new, do it with your 2nd bike and work towards that 2013 ZX6R or other brands.