Congratulations on your new purchase. I wish you a lot of luck. This is a huge project. I visited your blog and I sure hope that some of it is tongue in cheek. If I read your S.O.'s comments correctly and interpret the photos, you are planning to essentially, more or less, build a new boat (less the hull/bulkheads and rig) between now and July and then take off from Miami and head across the Carribean to Guatemala during the heart of Hurricane season. I sure hope that you are highly organized, have lots of cash, lots of boatbuilding experience, lot of energy, and/or are prepared to look at your scheduled July departure as a very loose goal with the serious intent to leave in November after hurricane season if not this year perhaps next.
One word of advise, as the Gulfstar 36 Motorsailors (BTW, you do know that these were motorsailors, and not really pure sailboats) left the factory these were not exactly robustly constructed- offshore capable vessels and so I hope that you are planning to beef her up some, replace the 35 year old lexan ports, and add better deck hardware.
I think I did some work on one of these back in the early 1980's, and there was an issue where the rudder post comes through the hull. At least on the one that I was aboard there was minimal reinforcing in this area and so there was cracking that was weeping around the base of the rudder post shaft log. So you might want to add a larger transverse and new a longituninal knee where the rudder post log comes through the hull and replace/repack the stuffing box.