When i read threads like this, newbie wants to trailer sail, mostly I think - this person has no idea what they are getting themselves into. And, what you don't know can hurt you.
As in - the boat is too small - Denise realized she needed more boat. most people just walk away from sailing because going bigger is financially out of the question.
PIA- that stands for Pain in the butocal region. A hour of rigging and unrigging can get old fast. That's if it's only an hour. Dealing with boat ramps gets old. Too steep, not steep enough, too slippery, too much current, not protected from waves, too much power boat traffic, not enough parking, did you remember to bring the keys to the boat? Where does the boat reside when not in use, did you remember to buy engine oil, what are kids doing while you rig and unrig load and unload, Daddy the bugs are biting me Etc etc etc!!!
Competing for time - if you have any time limitations to sailing a trailer sailor is going to sit in your driveway rather than get used. The time/pleasure calculation will always go against taking the boat out if there are time constraints. Especially once the PIA factor is added in. Example : you've got 5 hours of free time. 1/2 hour to prep for day on boat. 1/2 hour to reach ramp. 1 hour to rig. Same on back side leaves only one hour for sailing. Hmm?
The point being that there is much, if not accounted for, that can kill the strongest sailing dreams. Knowing what you are getting into before hand can go a long way in helping you achieve the dream.
On the practical advice side of things - 3500 pounds of towing means buying a 2000 pound boat max. trailer for a boat that size will be in the 800 to 1000 pound range and gear will easily take up the rest of the weight package your vehicle can handle.
If sailing just for you and your wife one boat not mentioned ( i think) Montgomery 15 and 17. Both excellent trailer sailors.
All the above is true and they're all reasons why currently I belong to a sailing club rather than owning my own (keel) boat. I do have an inflatable cat that's easy to transport and store but it's basically for sailing off of a beach and not very practical for more than two people. You're not going to sleep on the thing.
After sailing in the Apostle Islands on a 37 foot boat with members of the sailing club this past Fall I now have the desire to do some trailer sailing but still have all the same potential problems mentioned above. My wife isn't afraid of water but I'm not sure spending a week or even a weekend camping on a sailboat would be her idea of fun.
I do have a relatively inexpensive place I could moor it in the summer. There's room to park a boat in the driveway (barely) but getting it through the alley and around the ornamental trees would be a challenge. However, I am thinking that one of the trees is on its last legs anyway.
What I have found is that there is a huge variety of boats in the 18 to 26 foot range that might work. All of them represent a unique set of compromises. Some are easy to rig. Some a relatively light but tender. Some have more cabin space. Some have large cockpits. Some sail well, others not so much.
Anyway, I think the only way you're going to know for sure is to try it out, but yeah, learn to sail first, do your research on boats, and be patient. It seems like there are more boats out there than people that want them.