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Speaking from experience, look at the transoms very good on early to late '80's Grady Whites. Specifically the ones with motorwell cutouts in the transom. They were prone to water intrusion and transom rot. Not so much the case with full transom bracketed outboard models (which is what I ended up getting) or I/O models. Two other areas to look at on those are the deck inspection plates. Make sure the deck isn't soft surrounding them. Mine wasn't soft, but I removed the inspection plates and epoxied the cutouts like the factory should have done anyways. And check out where the cabin bulkhead meets the deck. Make sure that isn't starting to rot.
Beyond these points, there's not much else major in regards to structural issues. The 22' Seafarer and 24' Offshore are essentially the same hull. The 24' gains only 7"-10" (depending on model) of deck space. The rest is in the cabin. To me it was wasted space, so I went for the 22' Seafarer. The 23' Gulfstream is not really a trailerable boat without permits because of its 9'3" beam width. Very nice boat though. From what I understand, the '80's version of these needed twin outboards to track and handle well.
Good luck with your search.
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