Have kayaks too; I plan to get a small powered inflatable for shore runs from mooring buoys, and to explore smaller inlets. One of the nice things about the trimarans is the shallow draft, about 1.5" with the daggerboards up, so getting up on a deserted beach near high tide and waiting for the next high tide is possible.
I actually considered a property on Chokoloskee Island in Florida, the shallows and number of islands in that area are impressive and likely more challenging than I'd care to deal with, still not too far from the keys and Atlantic
No houseboats for me, but I still consider the "living on a big cat" option, but that really means selling (nearly) everything, and even older cats can be the price of a the average single family house, and need repairs, upgrades, refits, etc. which can get costly without even getting to the marina costs, and availability...many marinas have long wait lists, and some slips are for sale again close to the price of a house.
I'm keeping all my options open; I have a short list of boats I like, and I know once I buy a boat, the boat(s) at the top of my list will be for sale. If the boat at the top of my list showed up for sale at a good price for its condition, I'd start the buying process.
Not going to say what that boat is, but it's older, few were made, not all survived, and one shows up for sale every few years, usually in Malaysia or Greece or somewhere far (which means getting it here will cost $).