You need to do a lot of very careful investigations into what you really want. Spend a bunch of time going to shows, looking at
boats, and sailing (any way you can).
For a
live aboard you will most likely want the bigger boat, to sail faster, you will want the bigger boat.
For sailing in the gulf and around the smaller islands, you will want the
shallow draft. For ease on the pocket book, you will want the smaller boat.
For easy sailing, you will want the
roller furling for the
mainsail. But not for the faster sailing, (you give up a lot of
mainsail area for the roller furling).
My wife and I spent 29 days on the
water between Corpus Christi Tx, and Tampa Fla. we had a 2002 32 foot Hunter. At the end of the trip, my wife said we need a bigger boat and to plan a longer trip. So, I am back to
work with plans for a 42'
Island Packet in our future. 59' bridge clearance, and 5'
draft. Much better for the Inner Coastal
Water Way. (Our Hunter drew 5'10").