Mmmmm..... As a fellow S351 owner ('97 supercharged speedster) I think I'd hold onto the S351, and find another way to swing the Shelby. The S351's are ultra-rare compared to the Shelby, and I think history (long-term) will treat those cars like royalty. When they were available, they were the King Kong of muscle cars on the Market. Very expensive, very visceral, very obscure, and very heavily "built" (much more than just an engine, the S351 is chock full of trick parts from stem-to-stern). I feel that they are the Yenko Camaros, or Hemi Cudas, of the 90's. Right now is a lousy time to sell it, because they are at the low-end of the value curve, as it typically applies to aging collectibles. 10 years from now they'll be CRYING THE BLUES that they sold their S351 when they did, just as guys who sold their '87 Buick GNX's for $25K 10 years ago are now lamenting that the GNX's are trading hands for 70-80K +, and will continue to rise upward as years go by. The S351 will follow the same path as the GNX.
The GT500?? 8,000 per year, at least 3 years, it's alot of CAR, and it's far more refined and sophisticated than the old SN95 S351, but it'll never be the collector's rare and exotic gem that the S351's are absolutely certain to be.
Just my humble opinion.