I've had a PRIVILEGE 39 1991 for the last few years.
I used to take it out day sailing out of Brunswick Ga when I first got it to get experience. Best wind was 25 knots solo, it does great and is manageable. The boat is easy to sail and control.
I brought it around from Punta Gorda, Fl to Jacksonville last month. I wanted to get through the Keys by a Friday afternoon and the seas were 8-10 ft. NEVER again will l push the boat motoring into those or bigger seas. It sounds like a sledge hammer on the bottom. I have a hatch in the cabin that goes down in case the boat ever capsized and I found that is NOT watertight. Another thing added to my list to fix.
I've done one bottom painting and the boat is in pretty good shape. I found a surplus hatch a couple of years ago and we are replacing those one at a time, putting in solar vent fans etc.
The boat is easy to sail and has a decent reputation about being able to take it.
I looked at some of EXIT ONLY's videos on their circumnavigation before I bought this boat. Dave can probably answer any questions you have.