Planning a liveaboard boat in the future

Hey Jeff. Glad we talked you we talked you out of a watery money pit (living aboard). Let's keep it going. Run away from that $3,000 - $7,000 ++++ boat club as fast as you can. Freedom Boat Club has been around for awhile. They seem to appear and disappear and the boats are so-so, but their rates are a lot better than that other one. However boat clubs are a lot like gym memberships. First month you're all over it, and then your attendance fades when your boating day brings bad weather or life gets in the way. So don't stick too much money into it. Best bet see if there's anyplace that rents boats by the day or charter one around the size you're thinking about. Don't sweat the lessons. Boating is one of those things like playing guitar. Real easy to do but takes a lifetime and a lot of practice to master. Let me suggest you start your education with a USCGA or Power Squadron Basic Boating Course. The course is close to free and teaches you the basics, especially how to stay safe. You can even take it on line although I much prefer the in person classes. Once you buy a boat and depending on the boat you end up buying a 2 or 3 hour lesson will give you a wealth of knowledge and have you docking pretty clean. If you get a trailerable boat it'll save you a ton of money (assuming you have a tow vehicle), but the ramps can get real busy. DK what kind of facilities are near you. Check them out on Saturday morning. Just don't be one of those guys who launches your car. Next cheapest is rack storage. Boats kept on dry land start your savings with no need to bottom paint. Rack storage is mostly for open type boats under about 30'. You call up the day before and arrange the launch time. Having a slip is the most convenient way to boat and also exposes you more to the boating culture and socializing, and you can just show up at your leisure and go or just hang out, but it increases your maintenance and of course there's the slip rental. (Btw, a tip to the dockmaster can often get you on or moved up the waiting list. I'd suggest introducing yourself with maybe some fruit then show back up periodically with coffee and donuts, etc. while you feel him or her out for what kind of tips they get and let them know you'll take care of them.) If you decide to get a slip for your boat try to make a slip part of the deal with the seller. Easier done with a new boat from a dealer (which I don't recommend as the first year's depreciation is hefty and used boats you'll find get very few hours put on them), but always worth trying. I have a feeling there will be a lot of great deals on low use pre-owned boats under 36' next summer if the economy continues tanking, the large number of people who bought this year tire and hopefully Covid begins to fade and people start going back to other activities. Plus with all the fires I expect a lot of people will be too busy rebuilding their lives and homes next year to spend much time and money on their boats.

BTW, something to keep in mind: Big boats are impressive, but the bigger they are the less they tend to move. Too much hassle and expense. I used to keep a little 13' Boston Whaler in my garage. If I couldn't sleep I'd often pop it on the hitch, launch it at a little ramp by my house, blast around the bay for a half hour and an hour after I made the decision I'd be back home with the boat hosed down and sleeping like a baby. Now a 13' lacks creature comforts but I think you get my drift. Get what you need for the type of boating you want to do.

I know "it never rains in California", but you'd be surprised how the weather can stop you. How's the wind? Just a 15 mph wind from the wrong direction will chop up the water enough to make it a misery.
28' is a good size entry level boat but it's a borderline boat. You'll find that size comes with outboards, single or twin inboards or I/Os. If you go for inboards or I/Os I very strongly recommend going with twins. Yes it's more money for the 2nd motor and fuel burn, but it'll make docking and maneuvering in close quarters so much easier. Singles at that size, especially express cruisers, are like big sails in the wind. If you go for something like a center console with outboards single or twin is just a matter of how fast you want to go. At slow speeds you steer most OBs and single I/Os like a car (which can be difficult when dealing with wind). Twin screw you steer like a tank. One side forward and the other reverse and you can spin it on a dime. One back or forward and the other neutral and you turn on an arc. Remember that with boats at slow speed it's the propeller that steers you not the rudder. Rudders do nothing without a bunch of water going past them.
If you want to use a slip go back over what I wrote on tipping. Schmooze the dockmaster a little over the winter and you might find a slip opens up. I managed a couple of marinas and made serious tip money. I held pretty tight to my waiting lists, but some people were too nice (and generous) not to help out if I could, and some were such PITAs or so cheap that they kept slipping down the list. Also for dockage keep an eye on your local throw away papers with classifieds and sites like Craigslist for people renting out dock space at their homes. Bait shops are also good places to get leads.

I see the opposite. Smaller boats things are lighter and less labor intense (lines/fenders/shorepower cord). You also don't need an experienced person to play mate. And at night easier to dock a smaller boat with the better visibility usually. I see owners use their center console a heck of a lot more often. Especially on a whim, at 6pm they'll decide to lower the lift and take it to dinner.

There's more to leaving the dock than just handling lines. To start with there's the difference between 10 gph and 30, 40 or 100 gph. Then there's how much fun is it to cruise around alone or with one friend on a 50' yacht as compared to a 28' CC or such. There's what it feel like to blast around on a small boat at 30 kts + as opposed to cruising a big empty boat at 18 kts. And yes Pascal there's a big difference between handling a 50 amp cord and a 30 amp, like double the wait. There's also the difference in maintenance right down to a quick hose down after a cruise as opposed to washing a 50' boat. Then there's incentive. People are just more inclined to pop a small boat off the dock on a whim. Can you pop a 50' off the dock on a whim for a short scoot around the bay? Sure, but how many people actually do it? Also noted your statement that "I've lost track of the times we've been outside lately afternoon". How many time do you do that alone as tons of people with small boats do? It's just not fun.

Good range for a first boat. Depending on your budget and your cruising grounds I'd look towards the 28' to save you a round of 3 year'itis. (Year 1 'this boat is great. It's all I'll ever want'. Year 2 'This boat is great, but Bob's boat looks cool and he can handle bigger water than I can.' Year 3 you start shopping for something bigger and by the start of year 4 you've paid another broker's commission.) An 18' bow rider is good for the bays, fishing, water sports, an evening cruise through local waters with your honey, etc., fairly cheap and easy to maintain. Once you start heading for the ocean I'd be heading over 20'. A cuddy gives you a place to store stuff, a place to get out of the rain and a place where your lady friend can change or cop a squat. Not being familiar with your waters let me give you an analogy from here and a quick look at a map of Long Island, N.Y. will make it clear. Long Island is 120 miles long with about 700 miles of shoreline and distinctly different types of waterways on the North and South shores and in the fishtail out east. Where I am here on the south shore of Long Island, with shallow bays running from Rockaway in Brooklyn out to Southampton towards the east end (about 80 miles), an 18' is great. If you run aground it's no big deal and there are tons of bay side beaches and small canals to explore. Fishing close to shore on the ocean or around the inlets is no problem. But if you head out to the deep water a few miles off or if your cruising grounds are the north shore in long Island Sound where the ports are several miles of deep water apart, the shorelines are rocky and seas can kick up to a nasty 3' to 6' chop you'd want something bigger. When you look at a L.I. map check out Port Jefferson harbor on the north shore about half-way out. That's a great place to explore in a small boat, but it'll get boring by the end of the first summer and you'll want to get out in the sound where even on calm days you'll encounter 3' or 4' wakes from the big boats cruising by. In Peconic Bay in the middle of the fish tail towards the east end both big and small boats work. Lots of little beaches and places to explore in a small boat, but weekend traffic or weather can kick up a 2' chop that'll make an 18' bow rider uncomfortable. As long as you stay out of the traffic in the main channels you'll be fine in a little bow rider and there's plenty of water throughout the bay. Get in the main channel or around Shelter Island where the big boat are throwing big wakes and you'll want to be in something larger.

On Valhalla we had (2) 50 amp cords. Thankfully we had cablemasters, but they still had to be dragged down the dock. Maybe I'm getting soft in my old age, but they got heavy on hot summer days. 30 amp cords weigh like nothing. My 13' Whaler ran all day at WOT (about 30 mph) burning about 3 gals of gas, took 3 minutes to load onto the trailer and another 3 minutes to hose down. I also could always find a place to dock it wherever I went. It's all compromises, but I firmly believe in the KISS principle. Why deal with 50' of FBMY if all you need is a 28' cuddy. Also I expect the cost of 50' yachts to stay pretty constant because of their owner's investment and resources. They'll sit on them a couple of years waiting for the market if they have to. I expect some major discounts on used smaller boats by next summer due to the high volume of sales caused by Covid this year and people dumping them next year when there's other things to do (and after they paid for winter storage, etc.).

I agree with NYCAP- it's a big commitment for most people to take at 53' MY out and a lot more heavy work. Lines, fenders, 50 cord are much heavier than a 30 amp. Most people also need a skilled person to help them and get the lines, etc. Plus it's more of a job for people to concentrate running a larger MY and not fun for a short hop like a 50 mph 30' that they can hit the remote on their lift and start the engines and go.

Just a safety thought. If you decided to trailer make sure you have the right capacity vehicle, preferably brakes on trailer and learn to handle the extra load & different characteristics safely. Years ago neighbors married daughter was killed during a trip pulling a boat with the family to Florida. Reportedly it got away from her on the interstate. Be safe.

Add in that once a new boater gets to a certain size his insurance company will require he use a captain every time he leaves the dock.

Definitely grease the bearings, check the tires and lights and make sure you have the safety chains on. A friend uses a Ford Escort to tow his 26' CC with a 300 hp OB, but he rarely goes more than 20 miles. My neighbor recently bought a BIG RV. He has to hire a big truck and driver when he wants to go camping, and store it in a commercial yard. So far he's used it once. Right tool for the job is a must as is the right job for the need.

Just look over the side at the size, weight and number of fenders you have out unless you're one of those who cruise with the fenders flapping. A 28' going to Shooters would likely just lay his rub rail on the pilings. Now picture telling your new GF to deal with them (Stow them going out, and especially setting them out in the right places and ways when coming in). May not be a 2nd date.