Insurance is pretty high for me for a Stingray because Stingrays are collectible items.

 

my 67 galaxie insurance is dirt cheap, not only that but in Texas, anything 25 years or older is exempt from emmisions testing and i can buy antique licence tags that last 5 years and cost under $100.
the biggest issue i can see with driving an old car every day is simple operating cost for parts and labor to keep it running.

for performance and the low initial cost it is hard to beat a 92 or 93 corvette, they had the improved lt1 engines modern fuel injection, old enough to be cheap, new enough to look modern and efficient. give me a clean red or white on with chrome zr1 rims!