Swing keel or daggerboard for easier trailering.
fixed keel means the trailer gets top-heavy fast. It also means you need a steep boat ramp
where you can let the boat down into deep water
. A 16 to 20 ft swing keel boat can be launched with less than 3 ft of water
at the trailer axle. Fixed keel 16 ft boat might need 4 ft DEEPER.
I can launch my Vagabond 14 pretty much any place someone can launch a 14 ft Jon boat WITHOUT the outboard
Expect trailer to weigh about 60% to 100% as much (or more) as the boat for a daggerboard or swing keel boat. They have to be that heavy to be stiff enough. These small boats can be very light.
The trailer under my Minifish weighs 200% as much as the boat ready to sail.
Above 14 ft you'll probably be looking at mast
stays to rig when you raise/lower the mast
. That adds time and complexity to the process of getting the mast up.
Once the mast gets too heavy for one person to swing it up without aid of a winch
, you'll likely get tired of raising it and lowering it every trip to the lake.
Or maybe you'll move to an electric winch
... but be careful because those can break things if the lines snag.
Small boat "camping" can be like trying to camp out in a pup tent that gets bounced around by the water....
I'd want a 30 ft + for more than an over-nighter.
TRYING boats before buying
and learning a bit about sailing will give you more of a clue about what boat you might actually want...
What is right for me is definitely not right for someone cruising the Gulf of Mexico
I would want the 30+ ft (and probably 2 people with "blue water" experience) for sailing from Houston