The good thing about Whalers is they are almost infinitely rebuildable. Unless they have been utterly abused they are a candidate for repair. We used a 17' as a heavy duty work boat for years hauling firewood, fuel drums, nets, pallets of materials, etc. lots of rocky beach landings, left exposed all winter on some log skids. This boat was beat but every 3-4 years we would pull it, buy some fiberglass materials and go to work. By next season it was almost as good as new.
Rich S - the 13' and 15' boats had low freeboard and the 17' was a bit better but the 18' Outrage has plenty to be comfortable. The good thing about these boats, and I speak from experience, is they were designed to keep the engine powerhead above water and running while fully swamped. The only caveat being that the engine weight and assesories must be in boat spec.
The holes in the transom are fine. It is marine plywood and fiberglass, unless it was saturated for a *long* time it would be fine with the silicone patches. The hull patches are a bit worrisome, I have seen some horrendous work out there. What size are the patches? Whalers take a bit of special knowledge to fix correctly so who knows.
Is that the Craigslist ad for the boat? The 115 is a bit on the small size in my opinion but I always liked running Whalers a bit over powered, I had a 115 on my 17 and thought that was about perfect. That combo would be great for fishing and fuel economy, figure about 3-5 gallons per hour at about 24 kts. Not a ski boat but would be good for wakeboarding or tubing.