Hi John -
Good to hear from you. Welcome!
There are several folks on board here who live on and around the Great Lakes. Also, we have lots of friends down Florida way, so you should be getting plenty of comments. I'm out on the west coast (Oregon), and while I have been to Wisconsin a few times, I can't offer you much help.
CD 25 Cruiser? Yep - that's a good choice. It's just a little bit longer and wider than the CD 22 Cruiser, but a whole bunch bigger. The CD 22 is also one that you should look at real close. It is very easy to manage, both on the trailer and the water, and most owners frequently singlehand the 22. Towing the 22 down the highway is almost effortless with a standard sized tow rig. The 25 tows well, also, but needs a lot more tow vehicle to handle it safely (and a lot more room to turn it around if I'm driving!).
We just moved to a CD25 from a CD22, and the difference inside the cabin is amazing. How they can get that much more room out of 10" additional width is beyond me. We were very pleased (and comfortable) inside the cabin of the 22, even for the nine days and nights we spent aboard last summer around the San Juan Islands. We haven't spent a great deal of time aboard our 25 yet, but the one weekend we did get left a good impression on us. There is a surprising amount of room inside, yet the boat is still small enough to be managable.
You can't go wrong either way. If the extra size of the 25 is not a problem for you on the trailer, then it will be that much more of a blessing for you in the water. And really, it isn't so much bigger than the 22 that the road handling and launching makes much of a difference. Our first tow with the CD 25 was behind a Jeep Cherokee. It wasn't any trouble, really, but it was kind of spooky knowing that the boat was so much heavier than the Jeep. The next trip on the highway was with a 1-ton pickup, and it was a snap.
You'll be hearing from some folks closer to you soon. Have fun studying up! And if you're in need of a mini-vacation, the Seattle Boat Show that Jim mentioned is the place to have one! You will be amazed at what you find with this group of folks.
And, I think you picked an excellent place to post your message!