Reddit reviews Nigel Calder's Cruising Handbook: A Compendium for Coastal and Offshore Sailors

Start with the classic, "Sailing Alone around the World", by Joshua Slocum. I would also recommend some other older accounts, such as Cruising under Sail, by Eric and Susan Hiscock.

Get to know Lin and Larry Pardey and their books.

For specific advice on boat systems, see Nigel Calder's books Nigel is a very clear and detailed writer.

I have enjoyed these:

https://www.amazon.com/gp/product/0756689694/
https://www.amazon.com/gp/product/0071350993/

Edit 1 to add: Also, for entertaining reading, Joshua Slocum's book and Voyage for Madmen

Check out a couple of books by Nigel Calder. I recommend starting with Nigel Calder's Cruising Handbook as it's a pretty good general overview of everything you need to know for cruising, then try Boatowner's Mechanical and Electrical Manual as a guide to all of the stuff that you will spend all of your free time fixing and maintaining. I also have Marine Diesel Engines. He does a great job of explaining everything you need to know in an accessible way. He manages to get to some pretty advanced skills without assuming very much previous knowledge.

Hey friend. Pilot/Sailor here. There are parallels between aviation and sailing..absolutely, but my advice would be to approach sailing with the same independence with which you approached flying, initially.

There is an ENORMOUS body of information for potential "cruisers" available on line, luckily. I recommend that you hit the forums on Sailnet.com, for starters.

Boat-length isn't really the driving force behind your decision, so much as stability and ease of handling. Ease into the information you read through, and disseminate thusly which sort of cruiser you aspire to be. There are TONS of options.

Bluewaterboats.org
& this (basically a rod machado's take on sailing.)