Forget about how it was maintained. It's important but secondary. First figure what you want for amenities, layout & styling. Trailerable cruisers stuff a lot of junk into a small space. Most are laid out pretty similarly; but there are differences. For instance do you enter the cabin from the center or off to the side. That has a big effect on how things will be laid out both down below and on top.
Do what I did and walk through every cruiser you can. These are some of the boats I looked at B4 buying my '97 250 Sundancer. Four Winns Vista's(least favorite) , Larson Cabrio 254 & 244, Monterey 240 & 262, Glastron 24', Chapparral 240 & 260, Crowline 240 & 250, Chris Craft 24', Wellcraft 24' & 26', SeaRay 240 & 250, Mariah. I'm sure I boarded more. That will help you limit your choices. Mine came down to the SeaRay 250, Chaparral 242 and Monterey 262.
Here was some of the things on my short list:
No 5.0 V8's
No single prop drives.
No carpeted headliners,
No porta potties
No port windows that don't open
No boats w/bottom paint.
Your short list will be different but the one thing I strongly recommend is to not buy one with a single prop drive. Oh and the 5.7 in mine has all the torque that boat needs and then some. I knew that before I bought it because I test drove it. It's a cruiser not a performance or water sports boat.
For the years your looking at almost all/most will have a 8 1/2' beam. The big brother to my '97 250, the 270 Sundancer still has an 8 1/2' beam. You'll find that many boats this size don't have trailers as most people just slip them.
Good Luck with the hunt!