I have spent most of my time on the water for the last 20 years. It can work, but the practicalities are important. The demands and risks of sailing, coastal or blue water, are not really germane to your plans right now, except in a purely theoretical way. You want a home, not a romantic, exciting vacation. Your home will not move easily under the best of circumstances because day to day life grows stuff like coffee makers, TV's, computers, piles of clothes and paperwork and much more that doesn't brook bouncing around on the water. It will take _serious_ planning and saintly grace to sail your home regularly (once a month?) - not something to plan on.
You should be able to get a usable boat for $5-$20k. Without spending a very considerable amount of time reading and learning in any way possible, whatever you buy will be a crapshoot. Look through the classifieds in "Latitude 38" online magazine. It's one of the oldest boaters' community publications out there. Look through "Good Old Boat" magazine (don't know if they have an online version - probably); again, the classifieds. Those are the biggies I recall and there are likely other "live" info sources out there - it's been a long time since I read every word in every sailing mag. The engine will be the most troublesome and important and expensive thing on the boat. Without a good working engine you will have real problems getting a slip. Most harbors do _not_ offer the slip to the next buyer - you need to apply and sometimes wait in line. Next most important (if you want one) is the toilet. They rarely work as nicely as landlubbers expect and there are very serious laws about how they are installed and maintained. Read up. Did I say they don't work right too often? If you have a working toilet ("head" in boat speak) you will need to empty your holding tank regularly. If you're really sharp, and on top of it, you can drive your boat (this is something that needs an engine) over to the pump out station (incidentally, where is it?) during those hours it's open and pump you tank yourself. Alternatively, pay somebody to come by in a big skiff with an (almost) bigger tank on it and pump your tank as a service; you don't have to be on the boat at the time. Most upscale harbors have this service. Leaks from _above_ are one of your worst problems, given that you're not sinking, of course. They will almost certainly be one of the biggest PITA's you will encounter; they will teach you boat repair.
Lin and Larry Pardey who spent basically all their lives sailing, wrote the best book about _practical_ cruising I have read. I believe it's titled "Cost Conscious Cruiser". I mention this after saying that vacation is not where it's at because they give one of the best overviews of what owning a boat means.
Nigel Calder, "The Boatowner's Mechanical and Electrical Guide" is the best detailed review what's on a boat and how to fix it. This book is the one you need to deal with the necessities of life on a boat.
"This Old Boat" (the book) is a classic anecdotal review of the kind of TLC fiberglass boats need.
Brion Toss and Emiliano Marino both have excellent books about sails and rigging. But that's not really where you're at right now.
One thing no boat buyer ever thinks about is "how will I get rid of this thing... whenever". It's a very serious consideration because you cannot just donate a boat that is not in quite good shape. Marinas _will_ come after you for the cost of disposing a boat you leave on their hands and the Coast Guard will take you to court of you are linked to a boat sunk w/in 5 miles of shore. DO think about your exit strategy, know your options. Ideally, you can sell but life being what it is, maybe not. That's when you need to be smart. A boat is not as easy to abandon as a car. If worst comes to worst, the last quote I remember for "breaking" a boat in the SF Bay area was north of $4000 and that was a few years ago.
Wherever you think about parking your home, research long and deep (and quietly) the live aboard options. It's not clear sailing, sorta speak. When approaching _any_ person near the shore for information, try to _never_ use the words "live aboard" until you have (from several different sources) gained a very good idea who you're talking with and what their attitude is. Harbor masters talk to each other and many have a really bad attitude toward live aboards. So do the town council. So do the police and harbor patrol. IF you find a place where you can get a live-aboard permit and are willing to pay for AND can get one w/in a year or two (waiting lists...), then you're fine and set.
Provided... The boat you bring into their territory will need to be navigable (can't be towed in), insured (you mentioned that) and look half way decent or they won't take it. They also run credit checks. Your car will need a place to park and sometimes that is not as easy as you might think - check the details. Is the parking lighted? Do you have to move the vehicle every 72 hours? Is the area patrolled? Most harbors are not right across the street from a grocery store so will need surface transportation. Bikes are nice, but check carefully how you're going to park it. All harbors I have been in have rules that _nothing_ is left on the dock except the coiled mooring lines; enforcement varies widely, but "better" marinas tend to be more stringent. Placing a bike on the boat is possible sometimes; there may be bike areas on shore near the gates.
How is garbage handled? Are the gates to the docks left standing open or do they reliably lock? Are there "upwind" slips available. Stay in a downwind slip a couple weeks and you will see why. What are your neighbors like? Spend some time watching your prospective dock(s) from 6am to 9am and from 5pm to 7-8pm; also mid-day. One reason live-aboards have a dodgy rep is because they deserve it. As well as the rich folks with their water-skiing boats and day sailors, you find real hard cases bouncing along the bottom.
Necessities of life: VERY IMPORTANT. Drinking water and safe reliable electricity. Neither one is something you can just assume. Bad electricity will corrode important parts of your boat in the water; it's not always easy to get good information about this.
Internet. Not a given. WIFI is often claimed, often unusable. Test it from the location of your slip.
Right now I have a 35' slip in a marina 10 miles south of San Francisco in the bay. It runs me $300+/mo and goes up every year. Basic insurance I got from Progressive and runs maybe $150/yr. Don't recall.
Clothes on a boat. Casual clothes, not much problem, especially if you don't mind wrinkles. Office uniform... Problem. There is _very_ limited "hanging" storage on a 35' sail boat and suits will suffer.
Boat living is not really too hard, BUT: There is a learning curve that really doesn't start until you move aboard.
Cooking. A boat is a _very_ tight environment. Anything you cook "below" will be part of your atmosphere in bed that night. Thus a usable cockpit with a good "bimini" (large fabric awning cover) can be HUGELY helpful by giving you a back porch to cook on. In the rain and in blistering sun.
Speaking of blistering, ie hot weather. Your boat _must_ have decent ventilation (and depending on personal preference, decent light below). In practice that means openable ports that don't automatically let in the rain when open or require a fight to prevent leaks when you close them again. Depending on your location, bugs may be a problem - hence screens on all openings you use.
Well, that's enough talk. I like living on the water and (mostly) the people I meet are more to my liking than elsewhere. Though I generally mind my own business.
Ah, one other thing. If you want to sail, find a few boat clubs that sponsor races. Skippers usually need more crew than they can find easily and hanging around politely can often get you a place. Racing is THE way to learn to sail because a good skipper is working hard to get the most out of his boat; you see the right ways, the wrong ways, and the disasters and get some feel for just how strong a sail boat really is. Any good sail boat is STRONG! But they do break and it's nicer to find out what breaks them on somebody else's nickle. <g> In return for a good crew berth, you need to help with the chores on the boat, both on race day and often other times in the boat yard when things are repaired and maintained. Good racing skippers often YELL. There are some that don't, but when they are trying to screw the last 12" out of their opponent at a mark, things can get passionate. It's usually not personal, it can be really offensive and unacceptable, but mostly it's just excitement. Bounce around crewing or a few boats and find one where you learn and have fun. The position you start at is usually "rail meat": fit only to balance the boat. The highest position on the boat (barring skipper and navigator) is "fore deck" where you set and douse the spinnaker. One thing on crewing: Buy and bring your own life vest and foul weather gear. And take _everything_ out of your pockets when racing. A man overboard drill should really be done by every race crew, but... Nobody does it. Make sure your life vest works!