Best Boat to live in the harbor on

Same friend of mine also had and still has a Cape Dory 33 sail boat which he lived aboard for three years or so before he got the Grand Banks.

That was some spartan living, it was a bit cramped at times for him. So then he got the GB.
He just sold the GB last year and kept the sailboat. He also live on land now.

If I were you, get the small house inland and put $50 k down on a 36' Cape Dory , beautiful sailboat and own it . You can find them for that price in good shape. Nice layout and pretty roomy.
Or for less money and also a great boat a Person 35' .

Yes. Sea Tow and Boat U.S. operate in regions. If you break down in one region and have to go to a different region you can hit substantial expenses. We once broke down just north of Block Island. We were heading back to Long Island. Sea Tow Pt. Judith responded. and took us to about a mile from Montauk, but then had to transfer us to a S.T. from L.I. for the last mile or so. All the way home, free. That last mile or so was over $1,000. That said though they also saved my butt the one time I believed an owner about his fuel burn rate and ended up dry in choppy 6' seas off N.J. coming from Newport. They were Johnny on the spot getting fuel out to me (at no charge). So on that trip from LA to SF where you break down could be critical. You'll be towed into the nearest port in that region, even if it's in the opposite direction of where you want to go. Not sure if AAA works the same way as I've been lucky and rarely broke down in a way I couldn't fix or limp in from with both cars and boats.

We all dream. Then we ponder and learn. Like I told my wife the other day, I get a lot of good ideas. Not because I'm smart, but because I get a lot of ideas and the law of averages makes it likely that a certain % are bound to be good. If I told her half the ones I ended up throwing out she'd never sleep again. My career started right where the OP's did, to get a boat and live aboard. When reality became obvious plan B was to get my license, buy a boat and charter. When reality again presented itself I started running an LCM cleaning up oil spills in NY harbor, and the rest is history. The key though is to dream your dreams and explore your ideas before sinking your money into them. It's so much easier and less painful to learn from the mistakes of others rather than making them all yourself.

One type of membership will cover you on other peoples boats or if you own multiple boats, things of that nature.

I think it may depend on temperament more than anything else. I spend 7/10 months a year on my Nordhavn 43, and have spent Summers on a friendship sloop when I had a large Summer Cottage available. If I never spent another night on shore, I would be a happy man, but I have been sleeping on boats since I was a child, and have always loved it.
For an inexpensive liveaboard, I would consider a PDQ34.
Best,
Maldwin

My wife keeps me in line. lol.

Wow, you sure started young as far as getting your Captain’s License?
Usually folks needs several years of experience, as in Days of Sea Time, to get the USCG ticket, but one can always take the course and the test Without getting the actual ticket.
Quite a bit involved, not only multiple choice questions, but medical, drug testing, clean record, first aid and more. (Did all that twice as I let my first ticket expire, had to do everything again, don’t do what I did. )

If you are running a dive boat, it is usually required to hold a Dive Master License as well, not sure about the left coast, but at least when I looked for jobs like that in the Caribbean. (Never got around to it, Master Diver, but not Dive Master.)

Good luck.

It's a shame you and your dad never completed the course, and I sincerely hope you'll take it before extending your life to the water. It could easily save your life. I believe you can take it on line today. Contact the Coast Guard Auxiliary or the U.S. Power Squadron for info. But that's the Basic Boating course. It does not led to a Master's or 6 pack (Captain's) license. Getting a captain's license is considerably more involved including logging sea time on an appropriately sized vessel and a pretty involved test. If you get to a point where you want to go that route contact the U.S.C.G for current requirements. When I got mine 30+ years ago you needed 365 days of documented sea time within a 5 year period and the exam was 5 parts (and very few people pass all parts the first time through).
One more word on the Basic Boating Course, it's almost impossible to fail because the instructor's objective is to make you a safe and alive boater not to keep you from boating.

Actually what that operator's course did was sneak some knowledge into your head for you to draw on if needed. I took it as a child, and again with my wife when I got her into boating. She hated it and tried her best to fail. They wouldn't let her, and eventually she got her Master's license when I needed to hire another captain.

Definitely not, cause then you're responsible. That's why I never took my clients up on their offers to use their boats for my recreation. Just party on it and go home to your house that won't decay under your feet and will appreciate in value.

Those are my sentiments. I've had many owners over the years encourage me to use their yachts for my own personal use and I always decline for that reason. I don't want to be in a sticky situation, having to explain a situation. If something broke they'd understand that aspect. Only ones I've taken up on that offer were small center consoles.

I purchased my coursework from them and really enjoyed it. I wanted an online course as opposed to a one week intense classroom experience because I wanted to learn the material at my own pace so I could really understand it. It took me about 3 months to get through all the lessons. The videos were engaging and the material was reinforced through regular quizzes which I found helpful.

As someone stated, the test is challenging and the process to get all your medical documents about killed me (pun intended). But at the end of the day, coursework is no substitute for time on the water. It sounds like that might be what you need most at this point. Good luck!

This entire thread and forum is helping me with these same questions and decisions. It is actually leading me to a smaller boat.