Boy, opinions will be all over the map here. So, let me give you my story. As a CD watcher for decades and as I watched my 5 kids grow up and leave home, and retirement was at hand, I planned to strike the CD iron. I didn't retire wealthy, but I did retire with ALL my toys and home and debts at zero. That feeling, is in fact, better than sex. I've always had at least four boats of some type or another. My "big boat" was a mini houseboat and I managed to sell that for twenty plus grand. So, I thought I'd get a CD22 as a retirement present for myself. 7 days after that decision I owned a CD22.
I really wanted to stay in the 20 to 25 grand area for the CD. BUT, every CD I saw listed was no closer than 700 miles to my location in northern Utah. I have a LOT of glass boat experience both salt and fresh water, sail and power, and didn't trust any owner descriptions, and didn't have the time or resources to go check out all of the many CD's that are for sale 700 plus miles away from me at any given time. But I needed immediate gratification. By happenstance, an ad for a 2007 CD22 with twin 50 hp Suzuky's, radar, chart plotters, etc. etc. showed up 100 miles away within 7 days of my deciding to buy one. FOR TWICE the cash I had, but it was geographically close, met all my wishes, and was virtually new having only 50 hours in Florida Salt water and 150 hours on Flaming Gorge reservoir. In other words, it was perfection. Because I had half of the cash needed from the sale of the mini houseboat, and the CD was "perfection" I humbled myself and went into debt for the rest of the cash, and haven't regretted it a bit.
Prior to that time, I've never ever bought anything that didn't need work because I simply never could afford the near new or new. C-crazy didn't need me to lift a finger with one small exception. We put it in the water, everything worked and it needed nothing.
So, bottom line advice from my perspective is, determine how much cash/financing you can put together and buy the best boat you can for that price. I can almost guarantee that if you buy a beater, you will be putting way more money into make it ship shape than you will get out, and that assumes all of your labor is free. You are also at risk when you buy a "CLEAN BOAT." CLEAN is in the eye of the seller who is the only person who knows just how much "cosmetic, curb appeal" work went into the boat to get it sold. So, if you don't know a LOT about glass boats and systems, a qualified full marine survey should be done. Particularly with salt water slipped older boats.
My experience with CD's is limited to one year. Others here are more qualified. But maybe my story can fit into your decision tree as you think seriously about the CD, or any other similar class cruiser.