I've painted 5 cars(one I painted twice). After all my time, trouble, materials, and prep I would have been better off taking them to a dedicated shop.
He really doesn't want your business. Yes, it can be done for less, but you won't be happy about the job, and you'll complain later. There is really no such thing as a 'simple' paint job on a 65 car. There IS rust. There are dings, there is some waves in the hood or door, or trunk lid. Trust me, it's there, and as soon as he knocks down the existing paint, he's going to spend 10-12 hours on surface work. Block sanding is all hand work. I bought a pnuematic block sander, thinking it would be easy to get a nice flat surface. Nope, it's all about the hand holding the tool.
If he is a quality shop(sounds like he is), he'll pull all the hardware, and lights. May pull the windows and trim. Which means tape and paper to seal the engine bay, and interior and trunk.
Then clear coat, then wet sand, and finish buff. If you bring it to TX, and aren't in a hurry, I have a very good shop that will do what you want done for about $3000 or so. Another issue is the quality of the paint. Don't let anyone tell you all auto paint is the same. Reds, black and yellows have serious grades of paint quality that will be exposed after 2 years of sun and rain. You don't want to spend all that money and have it fade and chalk up after 2-3 years.
Might be able to knock it down to 3000 but not really with quality materials, that will last. All vintage cars have metal work needed. Right now I have a 63 Studebaker Avanti which is all fiberglass in the shop. I'm NO WAY going to try to scuff and paint it. I can already see some repairs on one fender, and once I start stripping it down, more defects are going to show up. You can't leave them and paint over, or it will look horrible. Don't just throw paint at it, get it done right, or sell the car. If it's a conv or FB, they will retain the value. If it's a couple, it'll never been super expensive due to the number built, but still worth doing right.
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