[Cajundaddy]

After owning boats continuously since 1975 I just sold my last one and am currently boatless. I will surely own another one at some point but in transition now and not sure how this will play out. All of my boating experience has been between 14'-40' both power and sail. To your questions:

1. Realistically what does it cost to buy, moor, maintain and operate a 35-45' used power boat that is of a quality that you might hope to not lose a ton of money over ten years? Or is there no such thing?

Boats are expensive to buy, expensive to maintain, and expensive to keep in the water. If you buy quality and maintain it to a high standard it will hold it's value better than most. Expect to spend at least $10k per year on a 40' trawler beyond fuel and mooring fees. A quality Hatteras 40 might be $100k-200k depending on year and condition.

2. Also realistically, how do you become competent and safe at operating said boat? Assume you're starting from zero.

Take classes in cruising and boat handling, make friends in the area and offer to crew with them often. If you can cook and clean you are golden. I currently crew on a Schock 35 sailboat and my weather, nav, and helm skills from 20 years of racing have value.

Personally, if you want to get into power boating buy a trailerable 20' outboard and take day or weekend adventures in rivers, lakes, and even sheltered ocean waters. Learn the ropes. Charter a crewed 40' motor yacht in the San Juans and enjoy a week on the water with someone else responsible for docking, anchoring, fuel, weather, tides, nav etc. This is a much better way to get up to speed and see if you like it than jumping into the deep end with a weight belt on.