Take advantage of the bad economy down south and find a fully done classic with lots of documentation and get at it. An all original/restored to original 60's car is as simple as it gets. They are way cheaper to maintain then modern cars with all the gadgetry and electronics. This is only goingto come out on weekends I assume so of you get a good car to start you'll probably have hardly any trouble. Try and find a car that was restored several years ago. If the paint is still good you aren't getting a bondo bucket. A poor job will usually show through in 2-5 years. A car that's been appraised is good because someone with some smarts had vetted the pedigree of the car and you know what it's value is.
My dream cars a 69 camaro and with the new camaros out it makes for an interessting decision. I could have my dream car for the same price as a loaded 12. Reliability, warranty, comfort, but that new car will be worth nothing in ten years and a 69 should be worth more. But a classic is a pain, you can't leave it just anywhere. I have a friend who has had people follow him home more than once in his 69, The emblems have been stolen right in a restaurant parking lot in the middle of the day. Anyway they aren't daily drivers for sure.
There are lots of clones of high dollar cars out there too, which is a cheap way to get a nice looking classic , and if something happens to it you aren't going to be losing something you can't replace.
Make sure you get insurance that will cover the appraised value and keep the appraisal up to date.
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