Late to the conversation, but:
"Why do we do what we do? As in what exactly are we after in the most primitive sense? And does it really matter how we attain it?"
Sounds like what you really want is one of the most badass cars on the block, you want it now, you want to be proud to be associated with it, and you want to wield it bravely.
You don't want to hide behind it like it's a social aid, or hold it over others like metaphorical superiority.
Only a small portion of this objective (albeit an important one) is fulfilled by the Hellcat. It's new, it's faster than fast, and it's ready to party.
What's left for you to do is own it. Own your ownership. Protect the joy that can come from it.
"Comparison is the thief of joy."
Comparison is the only reason your first post was anything longer than "Hey, guys, I bought a Hellcat."
Social division is one of humanity's signatures, and it's a clear and present hurdle in the car hobby. Domestic vs import, new vs old, budget vs expensive, built vs bought. We all pick sides.
But we all forget that all we're after is something that looks sharp and moves fast. And we're all part of every sporty car's target audience whether we accept the car or not.
You've grown to accept the car, and you've decided that you're able to afford it. Now just let yourself enjoy it.
No matter how "slow" the Monte ends up, it's still gonna look damn good. And no matter what others say, the Hellcat's gonna be as fast as the name implies. You've got family, you've got a life to live, and you don't need to clear any of that with us. I think most of us get so caught up dreaming up the exotic future that we forget about the present.
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Now on a personal note, I envy you. The Challenger is my favorite of the Neo Ponycars. And it brings me great joy to know that someone is going to give the platform a proper flogging in an autocross format. Every time I've run with a Challenger at Tire Rack, I've beaten it with my slapped together 216hp Buick Regal.
That. Should. Not. Happen.
So be sure to show 'em how it's done, Mike.