you need to check your SOFA, I believe you can bring your personal possessions with you that would include a boat bought outside the EU. The boat could then reside in the EU tax free, as long as you remain a resident ( and its not clear exactly when that ends). thats your best bet. i know many US service
personnel bring their cars etc.
As to cat/monos, my store of popcorn is somewhat dimished after the "cost of women debate and the zombie thread" !!.
You will pay a lot more to marina Cats, is thats your gig, especially in the western med where places are at a premium. If you want to anchor
out, then its not a problem.
If you intend to berth in Italy
, make sure you have a permanent berth first. They are scarce ( though the recession is helping free things a bit). Id do the rounds of all the marinas
nearby where you want to berth the boat and see whats whats. Quite a few marinas
don't allow liveaboards, but many turn a blind eye. Getting a permanent berth near where you work may be the most difficult.
As to flag, its matter not a wit. US would be the most logical if you are bringing in a US boat. Depending on the exact SOTA rules, you may have to follow local registration
procedures, these are fairly minimal in Italy
As to insurance
, YES you will need at least third party insurance
or you will not be visiting any marinas. Presumably you will be insuring it anyway.
Given the state of the second hand market, there are good bargains in the Med at the moment, if you can beat the Aussies to the boat!!. also buying
in the area you intend to live may mean you can work the berth into the deal.
I spent several summers in France
and Italy on my boat, finding a permanent berth has the biggest pain and one that I address as soon as you can.
( I don't know where in Italy you will be so I can't be too specific).
You'll love living in Italy , agh the food!! ( well not exactly the dining out experiences, for which France is peerless, but the ingredients at the markets, ahh I can still smell the salsa verde
and the quattro formaggio
sauce. ( damm wheres that Ryanair timetable)..
PS:you made need to establish a shore side convenience address for Bank accounts etc, Official liveaboards are somewhat of an anomaly and it may be convent to use a friends apartment as a address etc