So, let's see:

Weather: summer is awful. Winter is awful. Spring and fall both feature these three week intervals where the region is stunningly beautiful. The rest of the time you mostly want to keep your head down and your mind on other matters, which is probably what makes Boston so great for academics.

Amenities: All the advantages of living in New York, and none of the disadvantages of living in New York. More later. Just putting a stone in the soup for now.

It might help to have some background on said friend. The key points I would mention to someone from a small midwestern town would not be as informative/useful to someone from San Francisco. [e.g., rent/home ownership here is damned expensive, but not so much compared to NYC, LA, etc]

A combined Roberts Brain Dump Incoming...

Trees: There are lots of them, if you get claustrophobic it's bad, if you like pretending you're an elf living in the forest it's awesome. Either way you cannot ever really see where things are if you're used to anywhere in the western US. Open spaces are unusual.

Roads: Are insane and carved by cows in ages past. Get a GPS with a recent map update to make some sense of it all. Most roads outside of Boston itself are also not lit which is really weird to anyone used to most suburban streets being well lit in the west.

Renting: You can get some really interesting rentals and they aren't too expensive (in comparison to CA but more expensive than CO). Your best bet is often to rent a small house or part of a house. There are a lot of people who rent one level of a split level townhouse or something similar and you can find some of those that are really cool.

Living: Most places don't have a garage and that's a little weird. A number of places are heated by oil rather than natural gas or electricity which is also a bit odd. The RMV (Registry of motor vehicles) is the devil. Taxes are high and the tax laws rather confusing. MA does everything a little differently when it comes to government.

Other:
- Make sure you have a car that can deal with winter and snow.
- Have a snow shovel or pay someone to shovel your walk and driveway.
- Make sure to have winter clothes.
- You get Patriot's day off work.
- There is a yearly tax-free weekend holiday in August.
- Spring is amazing; Fall is beautiful; Winter is cold and horrible; Summer is hot and humid.
- Get an ez-pass for the toll roads it makes travel a lot easier.
- Good mexican food doesn't exist within 200 miles of Boston.
- Just about every other kind of food though does and it's usually pretty good especially the sushi, steak, italian, and chinese.
- There is a Dunkin Donuts on every block and their coffee isn't half bad.
- 5 Guys is *not* a good substitute for In-N-Out despite what people here say.
- There are a lot of excellent schools in the area.
- Communities outside of Boston are often very active for better and worse with lots of community events and things throughout the year. This also means you can be physically dragged (by the police) to a town hall if they don't have enough people to help vote on certain issues.
- Going to a baseball game at Fenway is a religious experience even if you don't like sports.
- Brunch seems to be a New England institution and so a lot of great places exist for it.
- Nothing is pronounced how you think, Worcester is "Whista".
- Very good or very bad is usually 'wicked'.
- A "Nor'Easter" is a wicked bad storm. In the winter it's probably going to be blizzard or worse yet, an ice storm.
- A microburst is a miniature, very localized tornado.
- Maine, Rhode Island, Conneticut, and New Hampshire are a lot closer than you think which makes going to Maine for lobster kind of awesome.
- No restaurant knows what a good avacado is or what to do with it.
- Driving in Boston is a pain in the rear. Parking in Boston is even worse.
- Small Farms and Farmer's markets are common and awesome.
- Strip Malls are rare a lot of smaller shops are re-purposed houses.

And lastly, Bostonians do let you know where you stand for better or worse.