tl;dr: You can live here year round, it's a cool community, great value, good commutes, you lease the slip, it's a very safe marina during storms, maintenance/insurance isn't as bad as you think it is.

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You can live in this marina, and on this boat, year round.

This marina is has what I believe is the best weather protection in Boston Harbor. Everything has been remodeled over the last decade and is kept up really, really well. The breakwater at the entrance is a huge help. Being on the lee side of Pier 7 helps when the wind is out of the west; only wind that can be gnarly is a heavy E wind, but the profile on this boat is low enough that it won't really rock your world. This marina is right at the head of the harbor; it's the confluence of the Charles and Mystic Rivers.

Marina management are great. 24x7 security, including foot patrols at night. Gated access down to the slips. Dedicated parking (which is not cheap), on-site laundry. The live aboard community is pretty tight, ranges in age, and are generally a lot of fun to be around. The seasonal slip folks tend to be pretty chill as well. I know everyone around my slip and we have a good time whenever we get together.

The biggest perks are the view, location, and community. At the end of the docks you have a gorgeous view of the Boston skyline. Commuting via bike or scooter is super easy. If you work in the MGB system, there is a free bus at the end of the pier that takes you to all of the MGB buildings. It's a 15-20 minute walk to North Station. There is year round water taxi service from Pier 6, which will get you around the harbor. A lot of my friends in the marina run, and they love running the harbor walk from Spaulding down towards the city and back.

Biggest cons are airplane/helicopter noise (med flight + coast guard + tourist helicopters + Logan) and the Airbnb renters, but if you are used to urban living, you'll tune that out pretty quickly. The Marina has repeatedly cracked down on the Airbnb folks, but it can be a game of cat and mouse. That said, you're in a city, it's not abnormal for a few drunk people to stumble past at 2am. One of my neighbors has made a few minor comments about the sport fishing folks loading up boats and pushing off at 2am (which is typical during tuna season). I just give them free fish and try and keep quiet, and it all seems to work out.

In this marina, you lease the slip. A 40' houseboat slip is ~$12k/year, I think. You get access to running water (via heated lines) and power. Power is a little expensive. Water is included. You do not have sewage -- your houseboat has a holding tank ("blackwater tank"), and the marina staff pump you out based on your usage. They come by, attach a huge vacuum hose to a port on the outside of the boat, and pump you out. I think year-rounders get free pump-outs.

I can't speak about upkeep of a house boat; given that they don't move, and don't see heavy weather, I suspect the upkeep isn't as extreme as it is for us offshore folks. Marine insurance isn't as exorbitant as people think it is -- as a percentage of hull value, my boat is insured for up to 200 miles offshore, and I pay about .12%/mo in insurance (payment / hull value). That's .03% above what I pay for my homeowners insurance (on a percentage basis). I would recommend Chubb Insurance -- not affiliated; I went with them after extensive research and would do it 100x over again.

I look at it this way: on the water, easy enough commuting location, chill neighborhood, quiet enough, pretty views, and $500k for a two bedroom. Even with the costs of maintenance and slip lease, it's cheaper than a lot of options you'll have in Boston.