FWIW,
After 7 years in our CD22 Cruiser, we moved to a much heavier more complex diesel/sterndrive 26-footer, for more room, and more/better creature comforts for our long summer cruises of the Inside Passage. It met the objectives, but certainly offered a learning curve in setting up properly, operating, and maintaining those more complex systems.
For the Volvo 44 engine, it was key to learn that it must be propped correctly to achieve full rated RPM at WOT with a full load. There were belts to check/change, impellers, how to do an oil change without making a total mess, more complex electrical systems, and many other details. I learned a ton from the boatdiesel.com website.
What I needed to have for spares, and how to change out failing items by myself in a remote location were super important. Fortunately mechanicing is something I usually enjoy, at least if I can get to the machinery (often not easy).
Took a big truck too, a 3/4 ton Cummins Dodge, to haul the ~12,000 lb boat/trailer. And keeping trailer brakes and bearings in good shape, towing thousands of miles through the mountains every year, was another learning curve and a good bit of work.
Much of my education came through experience. Sure would have been nice to have someone nearby to help me understand some things, but we're in Utah, and there aren't many boats even a little bit like ours here. Took a lot of time to figure my way though some issues, but I was retired, and had the time. There were some frustrating times during the learning curve, for sure, and after 17 years I'm sure I'm not done with it.
Was all this worth it? Absolutely - we've done a ton of wonderful cruising with the bigger boat. And I enjoy the learning/craft/hobby thing.