If any of you are moving to Boston or nearby with a car, PM me. There's a rather elaborate path you have to follow to get your car a parking permit. Especially if you're coming from a state where car inspections are a mystery.
I moved to Boston from Peoria, Illinois. I was like, "what the hec are those stickers on people's windshields? What's a car inspection?" Here, to the best of my ability, is a recount of what you have to do to park on the street in Boston or nearby neighborhoods:
1) get car insurance in Massachusetts
2) go to the RMV (the online site didn't work for me but you can try it...Google mass rmv) and get your Massachusetts drivers license and new plates for your car. I think you need to bring proof of insurance for this.
3) Go to a gas station that has a sign up that says it does inspections. They'll check your blinkers, windshield wipers, breaks, exhaust emissions, etc. If your car is in good shape, it'll probably pass. My car always passed. If you have any lights out or if your car is burning oil, you will have to make car repairs before you're allowed to drive it in Massachusetts. Once your car passes its inspection, the gas station will probably help you put your new plates on and give you a sticker on your windshield. Remember to get your car re-inspected every year! Some states only do inspections every 2 years (New Jersey) but Massachusetts requires it annually. If your car is caught with an expired inspection sticker it's a ticket for you PLUS a point on your license. So stay on top of that. My New Jersey friend didn't.
4) Go to your local town hall (Boston) or parking office (Somerville) and get a parking permit. You'll need to bring proof of residency with you. A copy of your rental lease (with your name on it!) and a bill in your name at your address should do the trick. Actually, just a lease has always worked for me, but that's not what the rule says.
Finally, if you live in Cambridge or Somerville LOOK OUT for snow emergencies or street cleaning days. If your car is parked in the wrong place at the wrong time, you'll get ticketed and towed. If you move to Somerville, don't park on the even side of the street when it snows. The snow emergency rules aren't posted anywhere and the city LOVES to tow and ticket cars. I was fortunate--I only got ticketed during the first big snowstorm in Somerville. You can sign up for email service through the Boston Globe to alert you the day before your street has street cleaning. I find that very helpful.
Basically, if you don't need a car, don't bring it. It's an ordeal.