You will love Italy, I moved here for work and live in Padova about 2hours from you. Heading to the dolomites or over to Umbria / Florence the rides are incredible, happy to hook up and go from some rides, drop me a pm or if you have any questions on moving to Italy.
For travelling, anything is possible, its an adventure. We got stuck on the Brennor pass for 18 hours last year mind, on a bike that would not be pleasant... There will be either rain big rain or snow and it will get cold or it will be amazing clear crisp days. As you know checking the weather before you leave is BS it will change by the hour up high. Snow has hit early whereas last year pretty much no snow. (Btw 3 ish hours from you is the nearest skiing)
But the right kit and the right attitude and it could be entertaining, make it what you want, prepare for everything as that is what you are about to get!
There is a Fantastic BMW dealership in Vicenza, Bellan & Giardina These guys know BMW inside out and backwards if you have any issues check them out.
Enjoy , great weather, great people, amazing roads oh and the food and wine is not too shabby either.