Hey Andrew - thanks for that. I gave her a call and she was really helpful.
Just to close out the post with the info I got...
I was basically told that it's quite hard for foreigners to get insurance in Italy and I'd have to be insured by an Italian registered insurance company. Outside of Italy Alessie could help insure me though the insurance would be very expensive (the same cost for all forms of scooter or motorbike up to the most powerful). I think it was around 750euro for 6 months or over a thousand for a year. This wouldn't include Italy but would include the rest of Europe. She advised me to look at buying it outside of Italy and then if the costs weren't prohibitive then they'd be able to consider by request (obviously they couldn't committ over the phone but I got they didn't expect any issues).
Hope this helps anyone else searching for something similar...
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