Goodness Idler, good plan!!! I have lived in Italy for many years now so I guess that I can answer some of your questions. In general Italy has awful public services and very very high car and bike insurance, for this reason I keep my bikes on UK plates with UK insurance and then change them after 3 years, to avoid having to come back for the MOT. Importing a bike and getting Italian plates is a nightmare and I would seriously NOT recommend it.

I would also be looking to rent a place to live initially and then buying later if all works out. Drop me a line on simon.f@spirometry.com if I can offer you some help. Simon

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(Now sold on, sob) 2011 Blue XT660X with gold wheels, was 26,500 km.
Engine mods: K&N Stage 1 filter, DNA Stage 2 filter, snorkel removed, Kev fuel mod fitted.
Plus: smoked Puig screen, Yam aluminium sump guard, Yamaha / Acerbis handguards, Givi Trekker aluminium side cases, Leo Vince X3 cans plus Kev front fork mod and Fender Xtender. Just fitted Michelin Road Pilot 3 tyres.

SOLD the XTX for a Super Ten 1200. And just bought a Raptor 700 so staying on here for some tips....