It sounds like you have the time, so take it while you still can. There will always be nay sayers, those that live in the comfort of not taking risks. The regret of not doing it will haunt you for the rest of your life.
As for the Vespa, it's up to you. I don't know much about Vespas, but I would prefer something a bit bigger to carry stuff. And bigger wheels for some of the rougher roads.
Good Luck!
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