Liveaboard and Cruiser
My name is Henry and your plans seem to mirror mine. I am 42 yrs old and getting ready to retire from the militay after 26 yrs of service. I will retire to Fl and want to sail the East coast and then over to the pacific and Hawaii. I like the Downeast 32 and Morgan 33. They have a lot of room and are strong blue water cruisers. A late 70 model will be in your price range.
I think buying a boat with or with out the electric goodies can go either way, just remember all the goodies in the world do not matter if they are over 3 yrs old. They do not count towards the price of the boat, and if the owner wants to take them w/ him then he takes all the plumbing too.