I was in a similar situation to you. My choice was to purchase either a brand new 2000 Corvette or a used Viper. I chose the Viper and glad that I did. Purchased a 1997 GTS blue with white stripes 11K miles in perfect condition. I drive it everyday, in fact it is my daily driver. I was surprised how comfortable it is to drive, even with all the regular street traffic. I have a short dive to work about 10 miles each way. If you do buy a Viper plan on upgrading the exhaust, the stock exhaust really does not do it justice.
After you mod your Corvette you may have a very mean and fast vett on your hands, but nobody will know except for you! Unless of course you do the occasional street race. With a Viper, everybody who sees it knows that it can eat up every other car on the road.
Corvette = nice car, good performance, over 1,000,000 total made
Viper = bad a$$ car, terrific performance, less than 15,000 total made
