I've had every gen except the 1st. I've also had 11 mustangs since 1987, including two GT500's, a '12 and now a'14, and have driven a GT350. I take your question to be, should you keep the gen2 with a gen5, or sell the gen2 for another / different ride.
IMO, as someone who has had 2 vipers at once, and a viper and a stang, I'd go with the gen5 and something else, especially with both being coupes.
I miss my '99 RT/10, but would I trade it for my 800hp GT500, nah. And the GT500 rip your face off muscle feel vs the gen5 sleek, road race exotic feel, play off each other so well. I honestly feel like I have the perfect combo between the two. The GT350 is a great car, but it isn't "quick" or "fast", to me it's too much in the road race category to be very different. The GT500 just has that slam you in the seat nd holy shXt kind of feel, even with the track pack & perf pack options, it's a muscle car blast with some manners. The GT350 is almost docile in comparison. So, I guess I'd say gen5 like you're doing, yay. GT350 I'd say yes, but something a bit more brutal would be even more "different", and I highly recommend the GT500, I'm biased, but they are so much fun and you'll never confuse the feeling between the viper and the GT500. And I can say the GT500 strikes up as many conversations at gas stations and grocery stores as cars far more interesting, and plenty of attention at cars/coffee. It's no gen5, but then that's what you want, something different.
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