Howdy from Texas!
I do not own a Corvette... yet.
I am about to buy one for my wife's 50th birthday and in my research ran across this great forum!
My second wife of 9 years has always dreamed of owning a Corvette. Personally, I've always admired them but not like she does until I started talking to owners. Man, are these things loved by their owners or what?! She finds the C5 more attractive than the C6 (headlights mainly) and loves the color of the 50th Anniversary Edition. I have been searching forever to find a nice one and when I do she always balks, mentioning things like car payments, insurance and such. I have come to the conclusion that she wants me to drive up one day in one and hand her the keys. That is what I intend to do.
I have located a 2003 Anniversary Edition Coupe, automatic (she has to have this) with 22,000 miles in pristine condition. There aren't many options on these, and I think this one has everything, including both tops and the performance rear axle (she doesn't care about this, but I am hoping I get to drive it once in a while!). It has BSM's and disc changer, neither of which I'd normally opt for. The owner was asking $28k but has agreed to sell it at KBB "private party" "excellent condition" which is just under $25k. Seems fair, but not a screaming deal. He has kept it garaged, is the original owner, and picked it up at the Corvette Museum.
I am struggling somewhat in that the 2003 C5 Anniversary Edition option demands enough of a premium over a base Corvette that I am very close to the price of a C6 with similar mileage. I have gathered that the C5's have better reliability but the C6's have slightly better performance and are quieter. But then what could be better for a 50th birthday than a 50th Anniversary Corvette! I am hoping that the Anniversary Edition will retain it's value a bit better when it comes to trading it in on a C7. In my dreams anyway.
I may be asking for trouble, but I would appreciate any advice!

Thank you!
You can't go wrong with either car but most who have had both agree that the C6 is a better car overall. Since you have a connection with the whole "50th" thing that may be the way to go, for YOU, plus you already know your wife prefers the looks of the C5. Best of luck, happy anniversary and enjoy the new car and the Forums. 



Good luck!
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