You don't say where you live, but if you're in the US and planning on any highway or freeway riding at all, go with the 250. It will have a GPS top speed of around 75, will cruise comfortably at 65, and should meet all your needs.
The one complaint I keep hearing about everything made by Piaggio is parts, and the problem doesn't appear to be going away. If the scooter will be your primary transportation, you don't want to be without it for weeks or months at a time while waiting on parts to arrive. A buddy in Charleston was without his Vespa for six weeks waiting for a part to arrive. In contrast, I recently had the drive belt fail prematurely, was able to get it shipped overnight, and was rolling again exactly 24 hours after the breakdown. Kudos to Kymco USA, Progressive Insurance who arranged the tow, and Speed City Cycles in Indianapolis for keeping me from being stranded from Wednesday until Tuesday over the long July 4 weekend.