Dennis,
This may be too late, but I thought I'd post for anyone else looking for information. I just purchased a 1991 model First 285 last season, so I can let you know the few things I've found on my boat. I haven't run into anything that would have prevented me from buying the boat. Most of the issues I've found are age related.
- It seems that there is a very slight leak in the transmission that I was only able to notice by putting my hand underneath the section where the drive shaft connects.
- There is a small leak around the pedestal which has damaged the wood in the aft cabin.
- I have some issues with the cabin lighting, but I'm planning on rewiring them with LED anyway.
- The navigation lights on the mast aren't working, but as with the cabin lights, I plan to replace them anyway.
- I have 2 basketball sized blisters under the cockpit that I am getting fixed when I get the bottom repainted this spring.
The rest of the issues I have are related to shortcuts taken by previous owners. All are things that I am slowly correcting as I have time and money. Overall, I think it is a great boat and I get lots of positive comments from others at the marina.
Scott