Newbie in need of advice

This is my first post to this forum. As per the title, I am a "newbie" to the world of trawlers and trawleresque vessels. Up to this point my largest boat was a 14' V hull that was originally owned by one of college professors that used it as a "personal" Coast Guard Aux vessel. That said, I would love to have any and all help in the following areas (and any other area you deem appropriate): Used vessels in the $40,000 - $85,000 price range; how to obtain information about courses involved in captaining said boat; classes on maintenance of boat; gas vs diesel; single vs double engines; ideas concerning doing the loop; insurance and tow (AAA for boats) pkgs; etc. I have read everything I could find on this forum and hate asking for repeats; however, I feel that it's imperative to get the most current thoughts and ideas from those of you with experience.

So far my boat search has turned up the following with designs that I tend to like: 1986 Present Sundeck 42,
1984 President 41 Dbl Cabin, 1980 Bluewater 53 Convertible, 1988 Marine Trader 40, 1981 Mainship 40 Pilothouse (SRG), 1979 Bluewater 45, 1978 DeFever Dbl Cabin (Called a Trawler and a Motoryacht?), 1977 Thompson 44, 1974 DeFever 40, and a 1987 Albin 43 Sundeck. I know you're probably saying: "This guy is everywhere with his likes!" I totally agree and for that I would refer you back to the word "NOVICE".

All in all I love the layout style of the 1986 Present Sundeck 42. At 67 yrs. young, I prefer not to have to climb a lot of extremely vertical stairs. Also love the idea of hand rails that are taller - I'm 6'4" if and when I can stand up straight. I also appreciate hand holds in the cabin areas. Aft main cabin w/ensuite head (electric preferred) and guest cabin fwd with guest head would be my choice setup. I seem to like the bimini/isen config. Love the idea of a non-slip surface. Basically - good layout and senior friendly.

Please let me know your ideas - they will all be appreciated (even the ones that I've read that tend to be a little "snarky"). Thanks in advance for helping this Bear find his retirement starting point!