I own an '04 C5 coupe. My wife and I bought it before while we were DINKS (dual income no kids) figuring it would be a car that we could enjoy for a long time.
If money were not object, I would have definitely preferred a mid-year (1963-1967), but buying an older car really wasn't much of an option for us at the time. The dependability of the modern Corvette won out --- not to mention the fact that it's a comfortable vehicle to take trips in. Truth be told, for a long time it was the most comfortable car that we had for trips (a Vibe and Blazer were our other cars).
Last summer, my wife and I took the car cross-coutry (our last hurrah before having our first child). The car was great for the trip; comfortable, plenty of room for our luggage, respectable fuel economy, and more than enough power for the mountains.
Right now, prices are rediculous on the late model cars (the C5 and early C6) making them, IMHO, a great value.
As other have noted, which year you go with should be what you are looking for. If you want to see the purchase increase in value, then I'd suggest a C2/C3 (C3 prices are starting to go up). They will require more maintenance, but if you like wrenching, perhaps that is an added bonus. On the other hand, if this is a car that you just want to get out and drive in the nice weather, then I'd definitely suggest a clean C5 or C6.
A friend of mine has a spotless '57 that he is paranoid about leaving out (at car shows, he won't let it out of his sight and he doesn't cruise around in it much). He also had a C3 that he was trying to decide if he was going to restore, or if he should sell it. I encouraged him to sell it and pick up a newer car to enjoy. He did and couldn't be happier. He actually drives it around and enjoys it far more frequently.
As a side note, I'm not surprised to see people who prefer other vehicles --- hey, that's what makes the world interesting; it would **** if all you saw were one make/model of car. I am surprised though to see some of the harsh words, though.