Thank you Dad for the quick informative reply.   Sounds like the ideal
is to have a fun one for short drives and a fairly new one for long
drives but I doubt I'll go that extreme :(  .    I'll stick to the fun
one because if I bought a new one for the long drives I'll get too
many speeding tickets (too much temptation).

Dave is right mostly here in that "fun" is subjective to each person.  My
fun and your fun is probably different than Dave's fun and each other's fun.
So to tell you which one is fun is like telling you which place sells the
best burgers.

Fun can be a light car nimbly twisting through the curves where the ordinary
driving speed would be 25 -30 and you are doing it at 45-60.  Fun can be
launching from the lights to run the 1/4 mile in 13, 11, 9, or whatever
number of seconds you get the most excited about.  Fun can be cruising along
a lonely country highway, top down, and a million stars all around.  No
doubt, Jack Tempchin had a convertible when he wrote that song for the
Eagles.

In some cases, I find the C2s to be more fun, in others the C3.  I find the
performance of the C4s will shake everything before (I've never had time in
the C5s or C6s, but they will shatter the C4.) but I'm not so sure that the
feeling of "fun" is as much, as there seems to be more raw open feeling in
the earlier cars.  Still again, there will be those who disagree, which just
reinforces how subjective this all is.

One thing not subjective is price.  Few C4s will get close to $30,000.  You
can buy most in the $10,000 to $18,000 range.  Many good ones for less, some
incredible ones for more.  C5s are down near the $15,000 on rare times, but
most are in the $20s and up.  Mid $20s is probably a safe range to consider.

C3s can go from $5000 to $40s and more on rare models.  However, for your
desires, you can figure that you can be $10,000 +/- $5000 for a rubber
bumper C3 and $23,000 +/- $5000 for a chrome bumper C3.  The issue of rust
becomes much more important in the C3s and older Corvettes.  You have to
check the frames under the rear of the doors and the birdcage inside the
body.  The birdcage is a critical make or break a deal as you have a hard
time finding parts to fix and it is extremely expensive and labor-intense to
do so.

C2s can occasionally be found in the Mid to upper $20s for modified customs
from long ago which serve well as drivers and fun cars, however, you will
often take a lot of heat (not the temperature type) from other owners (and
self-appointed experts) on how you have "destroyed" the car and how it is
sacrilegious to have done such to a Corvette.   Otherwise, you can
frequently find them from about mid $30s up to $100,000 for most good C2s
that are not some extremely rare beast, which puts most C2s out of your
criteria.

C2s suffer the same rust issues as the C3, so learn these cars well or pay
an expert to go with you to inspect one.  $100 to $200 fee is not out of
line and it actually a big savings, considering that without that guidance,
you can easily make a $20,000 mistake.

Good luck and have fun.