Considering relocation to Como. Looking for advice (Milan)

I'm considering taking a position with a European company which is affiliated with my current job/company. I would need to resign my current position to take this position so I will likely be negotiating a contract.

Has anyone from the States ever done this?

The new company is small so it is likely I will need to do a majority of the research and request the things I will need to make the move.

My wife and 14 year old son (who is starting high school this fall) will be accompanying me. None of us have any Italian language skills but are committed to, and have started, learning.

Any info on potential pitfalls or things I should be highly aware of in considering this move would be helpful. (housing costs, owning/insuring a vehicle, schooling)

I've read that we could put my son into an Italian state school which we think would be great so long as he has the opportunity to learn in English without losing out on his education. Is this even an option or will we have to send him to an international school?

What about healthcare? I'm unsure if my company will provide any as they do currently since our provider is a US based provider.

LASTLY... I will be visiting Como Aug Protected content , Protected content work and to check out the area in consideration of relocating. I would be happy to meet up with anyone living in Como to get a direct opinion from someone on the ground.

Thanks in advance.
Keith.