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This seals it for me. Just my personal opinion here, but if I were $20K under water on a car loan I couldn't imagine even considering purchasing a new (or used) car just to get a couple of new features.

For what it's worth (and for the record this is a terrible bit of analysis to perform from a financial perspective), I doubt any lender would issue you a car loan with that much negative equity. Most lenders require a down payment because they know that your car will be immediately worth less than the sale price and they don't want to carry the negative equity should you default on your loan.

My suggestion (again, FWIW): ride it out with your current car. Use some of the $20K to buy shares of TSLA and revisit this whole thing in 3-5 years when the next refresh S/X drops.
I've rolled over negative equity multiple times, it really depends on the lender and how well qualified you are most would say yes to an 800+ CS with proof of great income. Now as far as from the perspective you're absolutely right. I wouldn't put all of 20k into just TSLA but I do own shares from them and I purchase their stocks along with other ETFs that I purchase weekly. I most likely won't ride it out longer than the end of 2024 or beginning of 2025 if I don't offload it by the summer. The plan is to get out from under it because the end of my battery and drive shaft warranty are coming very very soon. It'll be here before I can even blink.
 
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