A certified surveyor was doing his thing on a boat I was considered many years ago. After about 20 minutes, he said to me " Professionally I can't tell you to not buy this boat but if you want to tell me to stop the survey, just say so" I looked at him, understood what he was saying and ended the survey.
I was new at the boating game and as I later learned his suggestion saved me from buying a vessel with big problems.
There is no black and white answer to your question. For example, a vessel may have wiring issues but you are an electrical savvy guy and like to do things yourself, so maybe the problem is not a show stopper. On the other hand, you might not want to deal with issues.
So ask your surveyor as he or she identifies areas of concern to explain what the implications are and how big of a deal are they are. A good surveyor should be able to ballpark a cost to remediate a problem at least in magnitude of the cost range
For specific models of hulls and models of motors, research what you can to see if there are common problems. Yes wet transoms are an issue but in many cases wet spots in a transom or other hull areas may not be a big deal and may be easily addressed. Many buyers are fixated on the transom but there are many other areas that can turn out to be major concerns. Express wet stringers on the port side and hull delamination is one. F350 flywheel issues are another. You probably are aware of exhaust issues on some F225s and F250s.
A surveyor may detect evidence of a major repair that was necessitated by an accident or abuse. The surveyor should be able to tell if the boat and systems were cared for or neglected
A price reduction after finding an issue or issues may sound good but if the price drops a few thousand bu the fix might cost 10 thousand, it isn't such a good deal. I can't stress enough the value of a good survey done by someone with extensive experience on similar vessels.
You probably need a mechanic's survey also on the motors, don't skimp and don't used a mechanic or surveyor recommended by the seller or a broker.