First let me say "Welcome to CHR". I have been away for a little while with a broken arm and avoiding typing. That said, from your photos it looks like you have a terrific car with a lot of potential. What others have said about your priorities are true. Things cost money, but don't have to depending upon your level of sweat equity and skills. Doing your own work you could likely rewire the entire car for about $500 for a good wiring kit including the extras. You could get away for half that price with a cheaper kit, but electrical fires, especially inside the car are a bitch, so I would go with a good kit.

You mentioned chopping the roof 2 -2.5 inches. Certainly would make a nice looking coupe. If you have never done a chop I would strongly suggest having a pro shop do it. Better yet - don't do it. A couple of more inches can be very nice. Don't get me wrong, I am not against chopping. I have a 34 Plymouth sedan with a 4 inch chop. Looks terrific, not all that comfortable driving if you are over 6' tall.

My choice, and I am sure I might be in the minority, would be to restore the body to original ( love the roll down rear window) and modernize every thing else especially anything related to safety (brakes, wiring, suspension, powertrain). But then, the car is yours to do with as you choose. Regardless of what you do, always make good choices, then the regrets will be minimized. This can be a great and rewarding project for you.