I decided not to comment here about using a gen 1 as a DD because the topic is maintenance costs etc... but since you asked: This car you consider is not a 'vette. An early viper is quite a bit less refined than your 'vette and lacks basic commuter comforts like windows and a roof! The sound system is crap (not that it matters since the exhaust discharges just a few feet from your ear). Did I mention that most (maybe all) gen 1 cars leak in the rain? Some of them worse than others so keep a few old towels handy on that first wet experience..just in case. You should also keep in mind that these early cars really can't be secured very well and it's a simple matter to break into a open car. Consider, two guys could easily swipe your $15k hood in less than 5 minutes! Better hope Walmart has their security cameras on! Furthermore, there are no cool little cubby-holes to put your wallet, garage door opener, spare change or cell phone... The '95s and 96s do have a pocket along the front of the seat. Let's see, there's zero trunk space when the top's in it so it's not a grocery-getter either. I'm sure there are other reasons why you may not want to keep a viper as primary transportation.
I consider these among the reasons why I love the viper but they're also why I drive a different car for mundane tasks and commuting. The old viper's great as a second, third or forth car... because it's GREAT at what it was designed to be!!
Proof that it can be done!!