New engine
 

I recently purchased an '85 Super Sport and I'm pretty set on dropping a 350 in it. JasperEngines will do the build for about 2300, but what other costs should I be expecting?? The current engine has just over 163,000 miles on it, so what parts are going to need to be replaced due to wear?

Does it currently have the stock 305 with CCC computer controlled carb and distributor? If so you can reuse it all if you get a manifold to fit the Quadrajet. If you want to get rid of the computer you will need to get an aftermarket carb and distributor. Then you can either reuse the stock exhaust manifolds or add headers and dual exhaust... Lots of choices depending on what you want. You can reuse most of the parts from the 305 such as alternator and power steering, fan and electrical systems.