outfitting your boat yourself for cruising i feel is essential. you can''t call a mechanic up if you are 500 miles from land. knowing how all the systems work and all the wires , valves, pipes and switches are i believe is critical . i personally rebuilt kimberlite and have found many times when something broke - and they do break- i knew exactly what was necessary to repair it. for example--on my last trip south to bermuda we lost our alternator in a full gale in huge seas. knowing how to reinstall the alternator and circumvent the smart regulator allowed us to have electronics , refrigeration, running lights and autopilot for the balance of the trip. another time coming up from st thomas we noticed a lot of water in the bilge we quickly eliminated the obvious and found a leaking rudder post stuffing box. we easily repacked the rudder post box. not knowing about these simple things can cause a miserable passage.
on a location note, i bought kimberlite in st pete and found there were many good craftsmen on the west coast. it is also a nice spot to take off from. one boat i looked was owned buy an 80 year old man who made annul trips to the bahamas with his 80 year old wife. he logged 30,000 between st pete and the carribbean between the ages of 70-80. so i guess you can cruise from the west coast . its only a couple of days to the east coast and going through the keys is a nice way to start any passage.
bill seifert has written a book called offshore passagemaking and is a hands on book of how to outfit a boat for offshore. the best i have read. should be in the stores in october. he incidentally ran the tartan, then the j boat then the alden factory has made over 35 passages to bermuda and the caribbean and is a supervisor for outfitting and maintaining many world cruisers.