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Alright, I've "lurked" for a few weeks reading and learning. First, let me say personal preference is simply that, and please accept that my personal preferences in no way denigrate other models. They are all wonderful in their own way.
My idea of a great car includes a folding top, a standard transmission, and a reasonable level of reliability. In my search for an acceptable vehicle to replace my prior ride, I've determined that a C5 convertible is as close to the ideal vehicle as I can find that meets my needs. (We still have our 2002 Miata, but I'm 3+ inches above the design height for that car and its feedback is too much for a long road trip!)
In my long and chequered career as both an aerospace engineer and a financial executive, I have a decent understanding of aerodynamics, structures, and market dynamics. The C5 appeals to my aesthetic sense of proportion and style, and though I realize later generations provide both performance and luxury enhancements, the beauty of the C5 speaks to me in a way the later generations cannot match. (if I could afford a "show car", I would opt for a C2, but I want something I can drive, not show.)
My career was primarily in the Aerospace sector, for obvious reasons, but I did have two stints as CFO of auto dealership holding companies, and thus I recognize that the prices of used cars in general are affected by the shortage of new vehicles. A low-level friend in the industry tells me that this is the worst time to be purchasing a used car, and that in particular sports cars, especially Corvettes, are selling for substantially more than they were 18 months ago. That, combined with the necessity of giving my lovely spouse time to come to grips with having a Corvette in the garage, has given me the opportunity to delay my potential purchase until some time in the next year or so after chips flow, new cars sell, and used car prices swoon.
And thus I write not to announce joyfully my acquisition of a "new to me" gorgeous Corvette Convertible, but instead to thank all the contributors of this fabulous forum for the vast store of knowledge it provides. I'm a member of a number of other similar groups covering a wide range of topics, but rarely have I found one with such a high percentage of positive info compared to the percentage of negative "flame wars". Hats off to this group for which I am truly grateful.
Welcome to the Forum, Cork.
Great that information in the Forum has benefited you in your “which generation is right for me” decision process.
I believe you will really enjoy and appreciate the C5 once you have yours.
Two years after posting my intro, I've finally joined the elite club of Corvette owners with a nice 2003 M6 convertible. My lovely wife sat in it after I brought it home, looked around at the interior, and said: "It's a nicer version of your old '97 Camaro ragtop!". As a real driver herself, though, she will appreciate the differences over time.
One shot below, because the 50th convertible has so many professional photos out there. This photo may not be great, but I like it because this subject of the pix is mine! Still hard to believe when I walk out into the garage and it's there.
Prospective C5 Owner
Whatever you do, don't let her drive it, you won't be able to get back in the drivers seat.
Although it took me responding to a couple of zombie threads with a knee jerk reaction, I learned to look at the original date. 
