"Does anyone have a shortlist of necessary book for long-term cruising, ocean-crossing, and eventual circumnavigating?"
Here are some favorites:
For preparing and maintaining the boat....
1. Nigel Calder's "Boatowner's Mechanical and Electrical Manual";
2. Nigel Calder's "Marine Diesel Engines: Maintenance, Troubleshooting, and Repair";
3. Nigel Calder's "Cruising Handbook: A Compendium for Coastal and Offshore Sailors"; and
4. Bill Seifert's "Offshore Sailing: 200 Essential Passagemaking Tips".
For celestial navigation....
1. Celestial Navigation for Yachtsmen (paperback or hardcover) by Mary Blewitt;
2. Reed's Nautical Almanac for region(s) you plan to visit;
3. HO229 sight reduction tables for latitudes you plan to visit; and
4. a small computer program for sight reduction (PC Nav if you can still find it, or other more current)
For body and soul....
1. Pardey's "Care and Feeding of the Offshore Crew"
2. Some of the classic sailing books
You're right, you DO need both paper and electronic charts. Electronic charts of the entire U.S. are available free as downloads from NOAA. They are available in both raster and vector (ENC) format. You will have to purchase electronic charts for the rest of the world, as you need them. You will need an appropriate charting program to use them. There are several favorites, depending on your platform (Windows or Mac) and your personal preferences, needs, and pocketbook.
Hope this helps,
S/V Born Free