Scott--congrats on landing the Speedster! Iknow you are excited.
Your idea of having a good air cooled VW mechanic look it over is good. I got great help from such a person when I first got my car and believe me I had more issues than the average bear!
Gordon knows a lot about fiberglass repair and look in the knowledge section for info on that. You would think that a Chevrolet dealer could hook you up with a shop that repairs Corvette fiberglass. I don't know for certain that it's the same material as we have.
If the paint is in only fair shape consider a process called "color sanding" I had it done and now my finish is amazing compared to where it started. This might be done in conjunction with the spyder repair.
I'm looking forward to seeing that Speedster! Remember, it's NOT a Miata with all the modern touches but far more than a Miata!