David,
A lot to unpack in your information-filled note. A few thoughts, all totally my own personal perspectives...
1) You will need to figure out what works for
you. Individual experiences, skill levels, and aptitudes vary
greatly. There are people who jump into a 40-50 ft boat as the first one in their lives and do just fine, and others who need a lot of practice to safely handle a runabout.
2) It sounds like you're just becoming familiar with the world of mid-size power cruisers. There are many, many options and possibilities out there beyond a power cat and the couple of models you mentioned. Before plunking down a sizable about of money, go to as many boat shows as you can and crawl around on different boats. The Seattle, Newport, and Annapolis shows will give you tremendous variety to explore, as well as any TrawlerFest you can get to.
3) It's one thing to be able to comfortably and safety handle a boat when sea states and weather conditions are fairly benign. It's a completely different situation when things get hairy. Though 95% of your boating may (hopefully will) be when things are calm and easy, it's the other 5% where experience and training make the difference between a merely mildly anxious situation that turns out OK, and a 'poor outcome.'
That doesn't mean you need to buy nothing smaller than a 75 ft Bering steel expedition yacht, but be mindful of when things get nasty. Everyone says they never go out in bad sea or weather conditions; it's not what you choose to go out in, but what you might sometimes get
caught out in that matters. Bad endings on the water often happen when sea and weather conditions exceed either the ability of the skipper or the boat to safely handle. FWIW, the skills and experience of the skipper are almost always the rate-limiting factor; most boats can handle far more than the crew can.
4) Consider the old adage of
'buy the smallest boat you can afford and that suits your needs.' It's very tempting to buy the biggest boat your budget can stretch to. Especially when touring them at a boat show, marveling in the house-like spacious cabins. It's a completely different situation when you're trying to dock the thing in in cross-winds and opposing currents, drifting towards impending impact with something either hard and damaging (rock, piling) or someone else's expensive boat. Or the cost and effort of maintaining a bigger boat.
It totally depends on you and your skills and experiences. Think about if going from a 20 ft 2,000 lb center console to a 40 ft 30,000 lb trawler might be too big of a leap? Having a boat bigger than you feel comfortable handling usually isn't fun, and you might end up being reticent to take it out as often as you otherwise would something you do feel comfortable with.
5) Think about how and where you will use the boat. Inshore, offshore, protected waters, open ocean? How long do you plan to spend on it? How often will you have overnight guests? Will you keep it at a mooring and anchor out most of the time? Or at a slip and staying at marinas? That should guide you to what style and kinds of boats might be better suited for you.
Often things come up only after using a boat that weren't apparent at the boat show. Two things in particular, machinery access and deck space. Everything on a boat will need service or repair eventually. Make sure you can get to the engine and other machinery easily, without needing to hire a midget contortionist to crawl into tiny spaces inaccessible to normal sized humans. Likewise think about deck access to handle lines, fenders, fending off in locks, pushing off from hitting things, etc. Depending on your age and physical condition, make sure you can get to all parts of the boat easily and safety without having to be a ballet dancer precariously pirouetting on impossibly narrow spaces.
6) There is no substitute for experience. Chartering a boat is fine, but consider lessons and training. TrawlerFest usually has hands-on classes, though your actual on-water time will be short. Consider hiring a captain to teach you. It would be a relatively minor expense compared with the cost of a boat.
When you get your next boat, practice, practice, practice. Especially docking and close quarters maneuvering. Go someplace where you have room (and won’t accidentally hit anything) and practice touch-and-go approaches and docking, from all directions, with and against wind and current. Spend many hours, days, and weeks doing this. It’s like playing a musical instrument. The more you do it, the better at it and more comfortable you will be. Get to the point where using thrusters is optional and not necessary.
7) If you haven’t already done so, get a copy of David Pascoe’s terrific book on mid-sized powerboats:
https://www.davidpascoe.com/mid_size_power_boats_chapt6.htm
Most importantly of all,
HAVE FUN! Boating is supposed to be all about fun, including the shopping experience. Drive the dealers and brokers crazy with questions and time spent crawling around boats.
Good luck!
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