Another big sticking point is food resupply.
I did really well on my boat, catching plenty of Yellowtail, Mahi-Mahi, Wahoo and Yellowfin Tuna underway. In most areas Grouper and Calico Bass were a dime a dozen. That does a pretty good job of providing the protien. But what about Fruits and Veggies? You pretty much have to run the risk and come into shore and resupply. Unless you have access to a remote area this will entail purchasing or bartering. I suppose that some of that fresh fish could be sold or bartered to get your resupply.
Do you think you could also get other supplies through bartering? You will need a lot of filters for that water maker, lots of high strength rope for anchoring and tying up at docks as the sun beats these up quick not to mention chaffing.
Consider too some of the skills you will need. If you own a large boat and your not an electrican, you will be soon, I promise. SW is hard on electronics, especially connections and wiring. Do you sew and have a heavy duty machine? Its a good thing to have and a skill to know. The first time you have to pay someone to repair a sail or replace a dodger, I can guarentee you will get one and learn to use it. Mechanic? Man if you need one of those you will get violated at the boat yard! I didnt have too many issues with plumbing on my boat, thank God becuase you gotta have arms like an orangatan to reach a lot of it!
Lets talk about boats a little too while we are at it. Tug boats are great from a stand point of being defendable, but they are slow and use good gobs of fuel to power those huge potent engines. House boats are roomy, but are for very well protected waters only. There is a reason why you dont see many on the coast! Trawler Motor/Crusiers offer the room of a house boat, reasonable fuel consumption, but top out at 12-18 knots. They are pretty robust and can handle rough weather pretty well too. Most can be powered off a 200-250 hp diesel engine. Sport Fisher boats...there is a reason all the big game fishermen call them Battle Wagons! They are big bulky and roomy, but they catch wind like you wouldnt believe making handling a challenge at times, take a pounding when the wave action is up so one less than 35 plus feet is out of the question in my opinion. Even modest powered Sport Fishers have big powerful engines and consume fuel at a rate that will make you dizzy! Sail Boats, there are the Multi Hulls and the Mono Hulls. Tri Marans are speedy under sail. Thier narrow main hull will seriously restrict you on interior space which will be at a premium already. This means you will need a much larger boat than other wise. They are easily over loaded weight wise as well. Catamarans are a better choice in a multihull. They provide far more usuable room. They are fast under sail and can sail in the lightest of winds. They too can be easily over loaded as far as weight capacity goes. One great advantage they both have is the ability to traverse very shallow waters. Most only need only 2-3 of feet of water. They can easily be beached to do hull maintenance, so that you dont require a boat yard and a lift for Haul Out. In a SHTF situation this can be a huge bonus. Both are increadibly stable platforms in the water although neither are all that great in heavy seas. Reaching speeds of 15-18 knots is very realistic in a Multihull. Mono Hull Sail Boats are probably a good choice in a lot of respects especially those with a shallow keel. Foot for foot most will carry far more weight than a multihull. They handle rough seas much better. The displacement designed hulls will be considerably stable, but wont be as nimble in handling. Speeds in a Monohull are usually 7-8 knots on a good day. Sail boats are usually great as their hull design makes larger engines a waste and unneccessary. Most are only used for docking and manuvering at a harbor anyways. A 10-20 hp is usually plenty of engine for a under 40ft boat unless out to sea under moderately heavy head winds. If choosing a monohull I would seriously suggest and recommend CYS (Caribbean Sailing Yacht) for brand. These boats are build like a brick crap house making them a very solid although heavy boat of the semi-displacement and heavy displacement designs. They cost a bit more used but are very solid and durable boats that can take some hard use and abuse.
Sailboat size...depends up on the number of folks involved and the length of time you expect to be confined to your boat. Sure you can pick up a used Catalina 26 and a couple with a child can make do for a pretty good while. But realistically a couple on a Catalina 30 (w/shower...boats this size and smaller usually dont have showers in them due to room restrictions) would probably prove to be the minimum size with a boat in the 38-42 foot range being a much better option! Two couples could proabably do well on a 45-46 footer. More than that and I think you need to seriously look at a 50-60 foot boat. This sounds really large and they are but then I have lived on one for 7 years and speak from experience! The difference in 4-6 more feet of boat makes a HUGE difference in living acommodations and comfort, more than you can imagine until you are living aboard for a while.
Pay attention to the boats lay out above and below deck. Shoot for one that can be single handed if possible. After 40 feet you can pretty much count on needing at least 2 people minimum to get it underway and keep it going. On the interior, layout is paramount. The more open and roomy the interior the better. It feels larger than it really is, air can circulate much better, it can be better lit with lighting and from skylight/hatches. You dont want to be running an obsticle course when trying to quickly make it from one end of the cabin to the other. Bunks in a stateroom are much more preferable to a bunk with just a curtian and you will sleep much better. Dont under estimate that galley either! Get one with an efficient lay out and plenty of counter space, one with large deep sinks! The one on my sloop is L shaped and provided a lot of counter space and kept everything within easy reach. This made meal prep easy even under way while rocking and rolling. Even though I cook mainly in a wok, you will be suprised at just how cramped things can get when your meal preping. Buy cooking utensiles expressingly designed for boats. They are slip resistant, compact and store very well compared to the dishware you are acustom to at home. The head...look for one that has the toliet in the shower pan as a combination that still leaves enough room to stand. This makes better use of the space and makes taking a shower easier when the boat is rocking. I know this sounds odd but trust me on this one. Make sure the head also has enough room to facilitate changing with the door closed even if you are a couple and intimate. Just cuase you can stand in it doesnt mean its roomy enough to be comfortable. Get a grill that clamps/bolts to the rail of your boat. It gives you more cooking options for meals and variety. Its also nice to cook out side on a warm day as opposed to heating up the interior. Insulation, the more the better. In the sun boats get hot fast, in the winter they get bone cold even when it aint that cold outside. It will also prevent sweating if you use AC/Heat, this will cut down on mildew problems which can be huge on a boat especially in the warmer climates. If your in an area where there is fog, a radar is mandatory in my opinion, otherwise you will likely meet something by accident. In Sand Diego this can be an issue and its just about garenteed to be an issue in the PNW on a near daily basis for parts of the day. Consider a power wench for the anchor rode. In 50 ft of water you will be using at least 250 feet of anchor line. It takes a long time to pull that anchor up with a hand crank one and if you dont have "22 inch guns", you will after a few times of pulling up the anchor!!! A power wench is money well spent!