I never thought I would ever buy a new car in my life having always liked finding the sweet spot of depreciation on fun cars. But when I got interested in a Wrangler and realized just how much better it was as a daily vs the JK, I ended up making the (somewhat scary) decision to go for a 2019 thinking buying a new 2018 or 2019 would both have some depreciation issues but over time Wranglers seem to hold their value pretty well so paying $34k for one now with a good down payment + trade made surprising sense in the end. Took out a bit of a loan that I plan to pay back within the next 12-18 months. And the best thing is I don't regret it at all. Its just such a fun car. Think the only danger is how much you might end up spending on customizing it. Already a little bit addicted so need to calm down. Also the other thing I realized for what I wanted it for, I really just didnt need to spend $40k+ on a Sahara/Rubicon etc etc. The Sport S to me is a really fair compromise of functionality and value.