Ive been in this situation several times, I've even worked in Italy for 12 months so hopefully I can offer some sound advice?
1. Which part of Italy will you be working? Driving in Italy is, let's say, slightly different to what you'd be used to! Your car will collect any number of dings and scrapes from the Italian parking techniques, reverse sensors are just a pre warning to the impact that's about to happen, your beautiful S5 would soon become battle worn. Leave the S5 at home, put it on stands in a garage, put a dust sheet over it and forget about it, it will be waiting for you when you come home.
2. Your company is giving you a motor allowance by the sound of it, don't fall into the trap of using this to pay for a rental, it's dead money, buy a car there and use the allowance to pay for a new car, at least you get a return on it when it's time to leave. Not sure on the US importing rules but I'm sure they will have made it impossible to import unless it was made in the US?
3. Two years will pass by very quickly, it takes you a year to fully settle in and get used to life, make the most of your time there, you'll be surprised how quickly it goes. Trust me, I'm now 5 years in to my planned "make some quick money for a year" job in Dubai. Italy is beautiful, especially in the North and Tuscany, if you like good wines and great food you'll love it.
4. Buy a phrase book if you don't speak Italian, you may feel stupid attempting to speak but trust me, the locals will really appreciate you making the effort.
5. I've left a car behind on two occasions, first time I left it with family and asked them to drive it once a month, this was a pain for them and for the car, they had to wash it before they drove it, put chocks in the wheels as you really don't want to,leave the brakes on, deal with dead batteries, it's just painful.
Second time I put the car in storage, buy 4 identical axle stands, put the car on these, remove the wheels (this prevents both the tires from getting flat spots and the wheel bearings from bearing the load of the car for two years on the same point). Disconnect the battery or leave it connected to a solar charger or one of those storage chargers. Buy a nice cover, the Audi fitted cover is great and won't damage the paint and just leave it alone. It will still be a perfect car when you return.
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