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Options Available for US employees living in Rome

The small company I work for (~25 employees) is open to me moving to and working from Rome (assuming we can work out the legalities of it). I'm trying to do a little bit of preliminary research for them since they've been so kind to me in the processes so far.

We need to establish what our options are. I don't even know where to start though or who (what kind of person) to talk to that would help me and my employer identify the different options and make an educated decision.

The options I have pieced together so far (I'm sure some of them are wrong and others exists) are these:

Employee of US organization that happens to work in Rome
- I'm not sure this is legal, and if it is, what the tax laws would look like.

Freelance Contractor for the US company, living and working in Rome.
- I'm assuming there would be more tax burden on me here, and less on the company

US company sets up an "Italian branch" or whatever its called
- Probably expensive for them, but would potentially allow them to also hire Italians?

Separate company funded by my company and pursing the "Italian Startup Visa"
- Not sure my company can technically be an owner of this company though. They may be limited to a "investor" or something.

Does anybody know if I'm even close to hitting my options here. I realize that the type of visa I will apply for will probably shift depending what course of action we take above.

Does anyone have a clue what type of person my employer and I should seek counsel from to figure this stuff out? Or, has anyone here been in my place before?


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