Hi Randy,
Well as you know I've got a 92 LT1, M6 and simply love my car. The lines, the interior fit and how it handles. I keep talking about getting a newer one, but just can't do it.
That being said, it took looking at a lot of junk before I found a jewel of a car. Extremely low mileage - was 63,000kms when I bought it, so it was tight, no squeaks and handled very well. As a matter of fact, even with the amount of track time it has seen, it is still that way.
A convertible will have more body flex than the coupe. There is an x-brace on the vert to stiffen up the body.
The guys called it correct in terms of the power, slow down low but faster at the top end. It is a torque monster
Probably not all, but one of the big screw ups for GM in the LT1 ( if I remember correctly, was the first year) was the Opti-Spark. Not so much the part but it is located right below the water-pump, which is notable for leaking. Total PITA to fix and also an expensive one. A new one is in the range of $600-900, before the labour.
I was somewhat lucky that the previous owner switched out to an electric water pump, however I needed to replace the Opti-Spark during it's first tune. My tech was actually shocked that the car would run considering it was so corroded.
Parts, while not all that hard to find, they are expensive. Mine typically come from the states.
You definitely would need to do the C5 brake upgrade on the front of the C4. Just spirited cruising on the street, braking was an issue on stock.
Getting in and out, Mark is so right, not an easy feat and I would imagine it gets worse as the body gets older.
I've driven a C4ZR1, C5z06 and a c6 and found them all to be night and day. Still waiting to drive the C6z06
I will say, as much as the speed, handling and the bells and whistles the new generations have is sweet, I didn't get the thrill factor that I get driving my car. I am old school though, growing up driving muscle cars that you had to actually "work" to drive.
The c5 and C6, I found that it was just too easy, at least on the street.
Randy, I honestly can say that I don't think you can compare the two generations. It's totally a personal choice for what you want. Do you now want a car that is "easy" to drive for cruising or do you want a car that you have to "work". Do you want to be wrenching on a car that is definitely getting up there in age, and parts do wear out, or do you want some added comfort that the car you buy is newer and has a potentially longer life, and therefore most likely lower maintenance for the big stuff?
Also, what can you afford? In alignment with the above, you may pay more out of pocket up front for a newer vette, an older one may end up costing you the same if not more as you need to replace the expensive parts.
Depending on how you answer the above...
If you can find a gem like mine, C4 - 10/10.
If not, C5 all the way - 10/10.
Each generation of Corvette will bring pro's and con's. It is all about personal choice, as with anything in life. Don't get caught up in "keeping up with the Jones'" as I've seen, especially in the Corvette world. It is a battle no one will ever win. Go with what you want and please only yourself.
If you do decide to look at the C4, go for 92 LT1 or newer, actually LT4 even better and inspect, drive, inspect.
Even though I have tons more to say, think I've written enough
Good luck and use the expertise here Randy to help you pick out a winner, regardless of the generation.

lauri
PS..As much track time my car has seen, still would beat a lot of the local "show cars" out there in terms of condition. The C4's I saw at Performance World proved that.