Ok Antonio, here is my personal view, take from it what you will.
First, let me say, I will be surprised if your insurance isn't AT LEAST 150-175% MORE!
When I considered the SKY for my father and I , we also looked at Corvette's. It wasn't a Money issue, we were willing to Pony up up to $60K, if we really wanted to. I test drove many cars over 8-10 Month's, both used and new. I too love Speed and the sound of RAW 8 Cylinder power, I grew up with a driveway ful of my brothers friends with Corvette's, Mopar, Stangs, etc.
What I found about the Corvette that turned me off (and there wasn't much about it that did) was the sheer SIZE. It is bigger than you think. It is a LOT of Car to handle, and will be WAYYYY harder to recover in a situation when you under estimate it's power. The SKY is fast, but not really POWERFUL. The Corvette is RAW POWER. I would say take it out and test it, you may find, as I did, it is just too BIG for you. Coming from a MINI which is basically a street legal Go-Cart, it was way to big of a jump and NOT AS FUN.
So if you are more about Fast/Control keep the SKY, if you just want that raw V8 and are willing to handle the bigger car than consider the Vette.
ECONOMICS:
Now let's talk reality, I know you are doing what any good red blooded American Male does when he wants something, you are trying to sell yourself the "FREE UPGRADE" policy.
Let's be real, your car right now is probably worth about $25K TOPS in this economy, as a Private Sale. The Dealer will not take it unless he can make a few Grand on it. He probably will not like all the mods you've done, people do not like to see that on a used car, because they know how you were driving it. I would say the dealer will not give you a DIME over $23K. Now you have to lay out $7K +TAXES + Gas GUZZLER tax (not sure on a used car)
How about the difference in Gas usage, this is your everyday car, let's say (the way you drive) you will average 16 Miles to the gallon, (10 Miles less per gallon). Let's say you fill up 5 times a month, so you will fill up one extra time.
So $9,250.00 more for the car (+Gas Guzzler Tax, if applicable) Maybe $1K More a Year in Insurance (I am being real generous here) and maybe $750 (at prices right now, which are supposed to almost double by year end)in gas.
The Corvette will cost you Approx. $11K the first year alone (plus money to personalize/mod).
If I was you I would save up some cash and get the Mallett conversion. You will have a BETTER performer, a more rare car, and you do not get someone else's headaches and the way Higher Insurance!
Anyway, just my
Good Luck Bud!
And I agree with Jason, you will never have enough power, I am over that feeling, It cost me money over the years!