Hobie or Keelboat? Seeking Advice.

Car or dirt bike sums it up well. Totally different needs and vehicles.
From your original posting, I'd say you want a monohull. Why does it have to be a keelboat? A Hunter 18 or 22, a Flying Scot or another daysailer with a swing keel. For overnighting a trailerable boat, look at the Macgregors.
I would love a cruising boat too, but had to choose one boat. I chose a Getaway. Is it comfortable? No. You get wet constantly, it's cold, you have to wear technical clothing or a wetsuit. You are not going to be relaxing and enjoying a drink with friends on it. You are going to be getting splashed and clambering over the boat every time you tack. That said, we do sail with friends. We go out, blast around, have a great time, then put the boat on the trailer, and THEN have a drink at the bar and laugh about the day.
COULD you cruise a Hobie Cat? I suppose so. With a tent and sleeping bags, in a dry bag, strapped to the tramp. It'd be like backpacking, whereas a cruising boat is like an RV.
The Hobie is not a fast boat to set up. On a good day, my wife and I can get the Getaway from the trailer into the water in about 45 minutes, or if we are also setting up the spinnaker, about an hour. A little faster to take it down. I expect you could set up a trailerable monohull faster than that.

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Yet another Bob!
"Firefly" - 2012 Hobie Getaway with wings and spinnaker
"Sparky" - 1978 Sunfish (OK, it's not a Hobie, but it's a fun little craft)
Too many canoes and kayaks

Hmmmm. You really have me thinking. Maybe that is what I want. A daysailer.

Tarzan have you looked at the tandem island, 5 minutes to launch from a trailer and stores nicely in our garage. Which is un fortunate for my wife's car (lol)
Bob

I have not looked say a TI. There was a place in a Rockport that sold the Adventure Island and would let people demo it but a customer ran it into shallow water and damaged it. I wanted to try it after they got it fixed but they sold it before I could see it. I have seen the AI and TI at ACK but haven't been in one on the water.

When I see people hanging off the side of a Wave with their feet under a strap on the tramp, it looks like they are holding the mid position if a sit-up.

Like this guy.

http://youtu.be/fV-7tmZXHh0

Does it feel as much like a sit-up as it looks?

Yes, but that's the same position you are in hiking out on most monohulls. You sit on the gunwale, with your feet in the straps and lean back to flatten the boat.
I re-read my posting about my Getaway, and I want to back off a bit. I made it sound like it's all work, but it IS a fun boat. You DO get wet on windy days, but it's part of the fun on hot days. You need wetsuits or waterproof clothes on chilly days, but you'd want wind proof clothing on a monohull on those days too.
The wings on the Getaway (and 17s and 18 SX) are great-you can lean against them, sit on them, trap off them if you want to really push it.
Is there a sailing club around you where you could try different boats to see what you want?

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Yet another Bob!
"Firefly" - 2012 Hobie Getaway with wings and spinnaker
"Sparky" - 1978 Sunfish (OK, it's not a Hobie, but it's a fun little craft)
Too many canoes and kayaks

I was a member of the Bay Yacht Club for a year and got to sail on other people's monohulls, mostly over 30'. I haven't sailed on anything trailerable, nor on a Hobie of any sort. You would think that there would be an active Hobie group in the Corpus Christi area, but none that I am aware of. Maybe I should ask that as a separate thread to call attention to it.