predicting what these cars will be worth in 2020, 4 years from now is pretty hard i think.
i doubt it will ever be a collectors car.
there are too many, and it's not old enough. and i'm not sure most of this generation really care about cars.

for the short duration of when i owned my 2000, i enjoyed driving it, but i think the reality is; it was a 16 year old car, it felt old at times.
it was fun to drive,yes, and it was fast (VERY).
but compared to the 2013 honda i drove to day, it felt old -well, heck both of our current cars are 10 years old, and they seem like old cars, but they work!

there is part of me that sort of thinks that the "new electronics of the C5 will probably fall in the range of the "new electronics of the c4" and just be old and outdated.
if you live in an area where you don't need AC, these cars might hold their appeal more, but in the midwest, driving your car right now would be very hard w/o AC.
the funny thing about all i said above though-honestly in my area, still don't see a lot of c5s on the road, did see one convertible today, and one red coupe on the interstate coming home, that's a pretty rare moment as of late in seeing these cars!

 

OP, IMHO used Corvette prices will take a hit beginning this fall. We all know that Corvette prices normally decline in the fall and increase in the spring, but this year there's a new dynamic in play. Used C7s have been holding their price point at an almost ridiculous level. 2014, 1LT base coupes are selling for only around $5K under a new 2016, maybe even less of a difference. But that bubble is about to take a serious hit as the 3 year bumper to bumper warranty is about to run out on 2014's beginning late this year. Combine that with the expiration of 3 year leases dumping C7s on the market and you've got a formula for a drop in the price of used, 2014 C7s. That's the first domino. Second is the C6 GS and Z06. They will be affected by the fall in C7s prices and will also drop their value. The base coupe C6 will in turn take a hit with 05s, 06s and 07s falling, probably into the teens. C5s will also fall, not as much as C7s or C6s, but they will decrease in value. IMHO, you should be able to pick up a nice older used C5 for $12K, maybe even a newer C5 with high mileage for that amount this fall.
This is all just my opinion, but the two statements about C7s are not opinion, they're fact.

 

Hello Mike! I did the same thing about a year ago or so after losing some friends to serious injury and death while on their bikes. Got the C5 vert as a cost efficient way of still getting the open air experience for my gal and myself while being safer and more practical. Probably one of the best things I've done, re-introduced and rekindled my interest in vettes in a big way. Light years ahead of earlier gen vettes I have owned. I can't think of a better performance car buy than a well chosen C5. Have a good one brother!