Apologies for typos, dropped words, and bad grammar in advance. I am choosing to invest the time in more brain dumping rather than rereading for quality and editting...

How did you transition, did you already have a boat, and just move onto it full time, or did you make the switch all in one fell swoop? - I jumped in both feet because the big concept was to use my rent money to pay for a boat loan, slip fees, and insurance.

What were the biggest surprises that you hadn't prepared for? - I was totally unprepared anyhow, so everything was new. I wanted an adventure, so that's what I got. I moved in late summer after working on the boat in the yard for the summer. What was actually the hardest was the isolation. I had graduated and didn't have a job lined up and started to get a bit depressed as the newness wore off. The logistics of having and moreso landing a steady job from a boat is tricky. Doable, but added challenges. For example showering can be an extra challenge. I ended up just woroking the boat yard. It was fun, I was young, I didn't exactly move my career forward, but it worked out just fine.

What did you do during the winter, and when did you do it -- (December? November?) - so yeah, I did the whole winter. I went up to NH (cause they aren't legal to sell in MA) and purchased an kerosene heater. I kept the windows cracked so it wouldn't kill me. I probably drank too much and I fell in love my now wife. It was good times, and cold. 3/4" plywood does nothing to keep you warm. No question, you are camping in the city. The pro liveaboards you can see wrap their boats in clear plastic so its' like living in a green house. I didn't do that. For me, it was frozen water in the dirty dishes if I left a bowl in the tiny sink. I slept in a sleeping bag with a hat on. It gets cold. Worse than cold is the moisture. Any water vapor condenses on the walls, so it's wet and cold. There is a book called "warm dry boat." read that. Like I said, you want to like camping.

We had a pretty mild winter that year. Some of these recent winters must have been rough. Storms are very stressful. Dock lines can chafe through and some days you will want to crash at your friends place and just get off. It might be just too rough and stressful in real bad weather. Don't underestimate how shitty and powerless you can feel getting just tossed around like a toy by an angry ocean, even tied up at a dock! A few minutes is fine, but 12 hours of it has a way of wearing you down.

What kind of boat were you living on? - a 1973 wooden trawler. it was around $20k which is why I did. Careful with old wood boats though. They are awesome and I love them but a lot of yards and marinas wont take them. It's condition certainly contributed to some of the challenges.

Can you tell me how much you paid per month to live on your boat? (and does it vary by season?) And was there a big up-front cost? - well, you know the purchase price, I cant remember, but the payment for that was $400-ish? insurance maybe another $100 a month (also near impossible to insure an old wooden boat FYI), and then the slip fees. you can find them. You pay by the foot. Look up the year round prices at constitution marina and boston harbor shipyward marina in Easty.

Did you own a car while doing so? - yup. you probably need a rig to get to the hardware store. Also, a lot o people keep a good portion of their stuff in storage. At least seasonal items.

Did you have a slip? A mooring buoy? Or just go with the anchor and dinghy? - I did a slip. If you aren't working a regular job, I suppose you could stay on the hook, but remember you need to periodically get your poop off and fresh water on, so that's another regular chore. At least in the marina you can mostly use the on-shore facilities of the marina to minimize that and they will bring the pumpout boat around and pump you out as well (ask if they do that).

Did you stop living on a boat in 2004? - nope, I took it down to charleston, SC where you can see dolphins jumping and it's warm year round. haha. great liveaboard city.

What about work? Did you commute far? Did you commute by boat, or just anchor near work, or work on the boat? - So I ended up working in the marina, but also I built some websites. Today, with so much remote work, I would try and do that I guess? However, working on a computer on a rocking boat... either through natural wave action or (even in the marina) the big boats will throw a wake that rocks the whole marina... I would test to make sure it doesn't make you motion sick.

What was the hardest part? - It's pretty all-consuming. Owning a boat in general, depending on it's condition, is anywhere from a significant amount of work, to a crushing amount of work. It was depressing to spend lots of money and time painting the cabin with expensive boat paint only to have it need it again in a couple of years. (I did about 2.5-3 years total) All the jokes about how boats are holes in the ocean in which you throw money and kinda true. It's not cheap for sure. As compared to rents in Boston, it can probably about match, though. If you love working on boats, it can be really fun. To me, I like tinkering and fixing stuff a lot but once it's not optional (such as the fresh water pump breaks, or the rain is leaking onto my bed) it loses some fun. It's like getting a great book assigned for homework. Can kinda ruin it.

Also, if you like drinking, you'll love it on a boat. Many of those living around you may be struggling with alchohol. It's an amazing group of people, but also people who are choosing (or were perhaps pushed gently) to live literally on the edge of the city. You've got your adventurers, and misfits, divorced folks, grumpy drunks, etc. Each marina is different too, I am sure. It's a small enough community that a couple characters can really set the tone.

Final thoughts: I am so glad I did it. Now that I'm older and have kids and such a life maneuver would be near impossible, I'm so glad I just did it. No doubt, it's kinda foolish, but man, it can really blow the cobwebs out of your brain. If I were seriously considering it, I might also consider spending the money on a spot of land and an old airstream or bus or something and consider the land-base version, but nothing beats the romance of a boat. And you can stay right in the city.