I am impressed by your car too. I might just give up on my Three Valve Turd and start looking at 5.0's next spring. I'd like a GT500, but I don't think my other half would allow that.
Just like most things, you get the new technology that makes the newer cars just that much better.
Honestly, unless it was a 2013 GT500 I wouldn't go that direction. The 2013 obviously has the technology to justify one. But the older ones do not have anything special to them. And the Coyote is a better motor than the old 4V. In many ways.
A Boss would be the way to go. Especially since you like road racing the car. It is a better performer. And since it has a forged bottom end you can boost it when the budget allows.