Before I get in to it, the Boss is an awesome car. I love the design and idea behind it.
With that being said, before I ordered my 14 GT500 I had considered a Laguna Seca. I drove one for a weekend and it just wasn't doing it for me. If I was going to autocross it or take it around an actual track, it might have been my choice. The amount of torque, the "softness" of the transmission and the lack of a supercharger whine all played in to my decision of going back with a GT500. Maybe if I hadn't of had a 13 GT500, the Boss would've been enough for me, but after getting use to that, I just wouldn't of been happy with the Boss.
Coming from my 2005 Whipple charged GT to the 2015 PP car I can relate to you (kinda) about the GT500 and lack there of a supercharger. My answer to this equation is simple. I'm getting the 2015 pp and going to slap a Whipple or Kenne Bell on it an wham, Bobs your uncle.
Best of both worlds. Get a "track" feel car with more balls than the ball pit at your local Chucky Cheese. AND without every disease and germ known to man with said balls.