I'm in Idaho.. everything is a mountain lake. There's one marina in within about 200 miles, and it has 42 slips. There's about 1.5 million people within 20 miles of where I'm sitting, so if you do the math you'll realize that we all trailer. Everywhere. On the plus side, there are 5 lakes within 90 minutes, so there's plenty of room.
Having said all of that, I have a 19 foot boat because I haul it with a minivan. (Yeah.. I'm cool enough for a minivan.)
Looking around at the local sailing club membership, there are at least 30 boats in the 24 foot or longer range. Lots of those guys have huge trucks and need 2 hours to setup/teardown a boat. On the other hand, the 3 or 4 guys I sail with use your basic f150 type truck.. nothing fancy. The water-ballasted boats are great for that.
And the only piece of advice I'm smart enough to offer is this... I'm also a huge fan of buying extremely inexpensive 'first' boats... I figure about 99% of humanity will want a new boat within two years after their first boat. So it doesn't matter what you buy now. Go buy a $20,000 boat.. in two years, you'll want a new one. Buy a $2,000 boat.. in two years, you'll want a new one. On the other hand.. you buy an expensive boat now, you are going to loose money on it. First, you'll loose money because you aren't as familiar with the market as you will be in two years. Second, you'll loose money because boats don't appreciate in value.. they always depreciate. Course, the depreciation on a $2 grand boat is a couple hundred dollars. The depreciation on that $20K McFabulous boat is several grand.
Anyway, for what it's worth, in my very humble opinion, heck yes a trailerable boat is worth it! And if you decide to visit the great lakes, you can do it. Or take a week camping trip in another state? Go wild!
And like I said.. I do it in the foothills of the rocky mountains with a minivan.. so a guy on the plains with a modest truck will be in great shape
I'm just saying.