My first boat was a 88 Offshore with a 225 Evinrude. We used the boat quite a bit the first year, however we found a great deal on a 92 Explorer with a lot more options so we decided to move on.
Our Offshore was the model without the bracket, outboard hung on transom. This worried me a little with our (at the time) one and three year old children. I often feared that one of them would fall or jump off with that large cutout that would accept twins.
The boat handled the seas pretty well and we always felt secure. Just before I sold it, it was surveyed and was in great shape, no soft spots, transom was in good shape, no moisture issues (it was ten years at the time). On the 1987 boat you mentioned I would look real hard for soft spots on the deck, perhaps some moisture issues below the deck, maybe water in transom, etc. Depending on your boating knowledge and the price for the boat, I would consider getting a survey. The surveyor will cost you a few hundred, but he could potentially save you a few thousand...
