[callydrias]

I've only ridden motorcycles, not scooters, and there are reasons for that. At the top of the list are: I want to be able to go fast when the mood/need strikes; I don't want to look like a douche; and I suspect it may actually repel women. There are more reasons, but I'll let others elaborate.

I can't imagine my only transportation in NY being on two wheels. I live in Tucson, AZ and I don't ride much in the coldest part of the winter. It's one thing to be able to comfortably stand 45 degree weather and quite another to do so when you're generating your own 40+mph winds. You can get riding gear that might keep you warm enough, but I imagine it would be pretty heavy duty and look completely mismatched on a Vespa. Also, consider road conditions. It's a bitch to ride in precipitation or on wet or icy roads.

If you decide to 2-wheel it, get your motorocycle license first. Take a class through a community college or something like that. It will help a ton.

Regarding security, you can get a wheel lock for protection, but nothing can stop people from just picking up your bike/scooter and putting it in the back of their pickup.

Conclusion: Get a motorcycle if you want something to tool around on when the weather is warmer, but have something with doors for winter.