Having purchase a '64 GTO Convertible back in 1992 for $600 ('68 400 included, not in car, original Muncie in the trunk, interior trashed, needed floor pans and trunk pans...), I have some experience with what you are faced with.
Unlike you, I wanted it to be Pontiac powered and kept the original M20 in the car. It took 3 years, but in 1995 it was done and I was cruising. I stopped counting when I hit $20,000 - my wife just said 'Get it done so we can have fun.'.
I went with the stock replacement interior, added the console, wood wheel, found a numbers matching properly date coded 389, painted the car the original Cameo Ivory.
I was very lucky that I had two friends that were instrumental in the build. One was my body man and the other was a former GM tech who had his own shop. They allowed me to help where I could and did what I couldn't. As mentioned above, check out the frame. We found a crack right in front of the right rear wheel area.
What some people called a 'basket case', won 2nd place in the '64 GTO Stock Class at the '96 POCI Nationals, in 2001 took 4th place at the GTOAA Nationals and 1st place at the POCI Nationals.
You mentioned the midwest. I lived in western WI when I bought the car and now live in Rochester, MN. If you're familiar with the Iola Old Car Show in WI, my GTO has been a Blue Ribbon Car there since 1997. It has bee a feature car there in 2001 (75th anniversary of Pontiac), 2024 (Muscle Cars were the feature) and just last week (Red, White or Blue Cars were the feature).
I'm telling you all this to let you know it's okay to dream big. My dad sold Pontiacs from 1963 - 1997. The GTO was my DREAM car since I was 9 years old when the first one's hit the dealership.
In 2013 I replaced the 389 with a 30 over 455. I like the new engine.
I've now been driving my dream for 30+ years and have put over 38,000 miles on it.
Future mods may have me pull the M20 out and replace it with Tremec TXK. I would probably go with the 2.87 first gear version with the .68 OD to go with my 3.08 12 bolt rear end. That would give me an effective 1st gear of nearly 9 to 1 vs the current 8 to 1 and a cruising RPM of about 1800 on the interstate. This would be about 1400 on a 55 MPH highway, but my car still pulls fairly strong in 4th gear at 1400.
I wish you good luck with your project.
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