Doing this as a poll, but also would like your reasoning why you chose what you did. Here's the story: For lots of unimportant reasons, I've decided it's time to reward myself. I'm looking at the two options above, so not really interested in additional options. I was set on getting the Boss when the time came, until recently on a cool vacation in NorCal, where I had a blast driving a rental Corvette convertible (the 5.0 I reserved wasn't there, so they comped me). I had some awesome drives on some amazing twisties, and thought to myself that it wouldn't have been near as much fun if I'd had a roof over my head. If they made a Boss vert, I'd be set, but I don't see that in the cards. So, here's the pros/cons. GT 500 pro: *convertible *Shelby name (always wanted one, but to old and broke down to really enjoy driving an original now) *200 mph! (of course, I'll probably never be able to legally use it) *convertible (I'm kinda biased toward top-down driving...) GT500 con: *about $20k more than the Boss *color (Candy Red) wouldn't be my first choice, but I do like it. Boss pro: *Boss 302!!! (always wanted one of those, too..., but not enough to name my daughter "Boss". So technically, I have had one Shelbi. ) *$20k cheaper (not a deal breaker, but it is a lot of money!) *Color (School Bus Yellow!) *I'll still have the 67 for top-down days, so it's not like I won't have a convertible option (95 is on C-list though) Boss con: *not a vert. (duh) Car will be a summertime daily driver, stored in winters. Not planning on racing. When I move back to L48, it will be driven year round as a DD, unless the weather's crappy. What say you, StangNet? What would you do, and why?