Sailing a Serious Ocean - John Kretschmer - Great stories and a ton of valuable information in a really easy to read format. It's kind of strange how it's all put together with in depth boat design mixed with stories, but it makes it really engaging. John seems like a good guy to have a beer with.
The complete Rigger's Apprentice - Brion Toss - What else can you say that hasn't been said already about this book? After missing Brion every time I stopped at Port Townsend, I was finally able to stop by his shop a few years ago. It was obvious he was going through some serious health issues, but the shop was in great spirits. Family was there, kids were playing, a few people were sitting around talking about all things sailing and rigging, it was everything I had expected after reading a few of his books and listening to some podcasts he's appeared on. Of all things, we ended up talking about tube amps. I was so impressed with how open and inviting everyone in the shop was.
Boatowner's Mechanical and Electrical Manual - Nigel Calder - If you don't feel like going down the youtube / internet rabbit hole to find a solution to whatever mechanical or electrical problem you're having, this has been my go to book.
Pleasure Boating Sail and Power - This one's a bit of a weird one because it doesn't have that much detailed info, but it's important to me because it's been in my book shelf from when I was a little kid. I don't remember getting it, it was just always there. I've read it cover to cover multiple times growing up and have found myself picking it up randomly and thumbing through the pages. A few years ago after my dad passed away, I picked it up and noticed an inscription inside the cover that I never noticed before.