One other thing I don't really get is that it appears that you'll be working during this time, it is not a vacation...so are you sure that 2000 km/month (what you've been quoted for vespas) is unreasonable? Your trip to Crater Lake was 12 days and less than 1300 kilometers, and presumably you weren't working during that trip? I don't know how fast you can travel on a vespa, but presumably you'll be avoiding the highways to it could take you a full day to go a few hundred kilometers. And having spent quite a bit of time in Italy myself, it is not a place where you want to be riding every day...go to a nice new town that you find, stay there for a few days to get your work done, then go another few hundred kilometers. If you plan to spend a week at a time in one place, then the calculus seems pretty easy, especially if you can average your kilometers over the entire rental, rather than per month (as seems likely).
I don't know for sure, but I would expect mileage overage fees to be pretty steep, because the vehicle providers probably intend for their scooters to be used to cruise the piazzas rather than the wear and tear associated with high-mileage usage. That said, 500 euro a month is an absolute bargain, so you're starting in a good place.
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