... ABACOS 101 I say ... the Abacos are an excellent place to get one's feet wet. Not my first choice, but given what you have said, Marsh Harbour area would be ideal. Lots of, and easy flights in & out, a few marinas in Marsh Harbour that will happily look after the boat, or if the owner wants, he can put the boat on a mooring in Hopetown or ManOWar (Edwin's would be my choice) and have someone look after it. The Sea of Abaco is easy to navigate, protected, 5.5 of draft is not an issue here really, he will learn to follow the tides, there are plenty of cruisers around to help them out, the cruiser's Net in the morning is a great resource & intro to the area, there are tons of things to do and places to go. Just like South Beach but only the Bahamas. I suspect this fellow will like the fact he can feel like he's world's away, yet the have the conveniences and safety at his fingertips. He can leave Marsh Harbour in the morning, sail to Great Guana and Nippers for a pig roast or lunch at Guana Beachside, then if the tide is right, go into Hopetown Harbour, grab a mooring and walk around town all night listening to RakeNScrape. If he's feeling adventuresome and the weather is right, he can skip across the Whale, spend a week or so bopping up the north side to places like Green Turtle, Munjack, Allens, or even Double Breasted Cay, where he won't find as many boats, yet have all the protection & comfort he wants a day's sail from Marsh Harbour. Or they can travel inside or outside down to Pete's Pub, Tilloo or Lynyard Cay, anchor out a few nights with no other boats around. Again, where they'll feel like their off on some Tahitian island, but haven't cut the umbilical cord. Diving & snorkeling in the Abacos is excellent, as are the beaches. Provisions, boat services, shopping, restaurants, whatever are readily avialable. After a year of this, he'll probably want to check out places like Eleuthera, the Exumas and Out Islands, while getting a fair bit of experience under their belts, how to read the water, what it's like navigating Cuts in the Bahamas, and where is best to anchor and when.
If there is a hurricane coming, he will have choices ... a mooring in Hopetown or hauled by Abaco Yacht Services in Green Turtle being a couple. Fresh water is not a problem in the Abacos, every marina has it, generally for free.
Unlike Nassau, which is a dump, he will have endless daysailing opportunities in the Abacos, he could spend a year doing that and not be bored. And his boat, his dinghy and whatever will be safe. It is friendly, he will develop relationships, and will get to know local folks.
Only two books to get ... "Explorer Chartbook for Near Bahamas" by Monty & Sara Lewis. And Steve Dodge's "The Cruising Guide to Abaco 2011". Don't bother with anything else, these are the best.
Cheers, John