Don't forget a chart plotter AND paper charts for your areas. Chart plotters can leave out some very pertinent information that is on the paper charts; things like shoals and rocks come to mind.
You should think about getting a SAT phone as well since you might want to email your friends or get weather info. In most areas of the LIS you will have cell phone connections but it is nice to have the backup and computer hookup.
Did I mention an auto pilot? Below decks control of the rudder seems to be quite a lot better then the wheel pilots (had the below deck auto pilot going from Tortola, BVI to TCI (Turks & Caicos) with no problem over 400 ocean miles).
As for bottom paint, I do it every year with a cheap ablative paint. If you want multi-year performance you will need to spend about $200+ a gallon for the better stuff.
The marine growth on things like the propeller are always a problem. Plan on having someone dive the boat to give it a good cleaning at least once in season. The cleaner the water is the more critters there are to attach to your boat's bottom. It does not take a huge barnacle build up on the prop to reduce it's efficiency.
Average yearly cost for a 40' sailboat would be conservatively $4K/year not including upgrades, fixes and fuel. I would budget for more if I could afford a bigger sailboat then my Tartan 27'.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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