1. Do you mean a special charger? If so, yes, we did, but it was years ago. I don't remember the cost. The level 2 charger is a lot faster than the regular outlet. I usually just plug in at night, but I don't need to do it every night. The times it really come in handy is when I plan to do a longer trip, so I can push it to 100% and have it ready in the morning. If you have space for a charger, I highly recommend installing one.
2. I do have a tow hitch, but I haven't ever used it.
3. Insurance is about 750 a year with State Farm.
4. Have fun! It's our 2nd Tesla, so I pretty much knew everything about it already. It will be funny, though, when you get into other cars and turn on the wipers when you intend to start driving.