It's not easy to swap from a Y-block to a Windsor block. In my opinion, I'd stick with the Y family and simply go bigger.
If you're gonna keep the 302 idea, swap the cam, as those aren't too great from the factory. Get a 302HO truck/RV cam from Summit Racing and call it a day. It's a roller block in the '86, so make sure you get a hydraulic roller cam if you go with it.
The carb is easy to do, just get a 4bbl intake and a good Edelbrock carb (550-600cfm, no bigger).