This seems like a great spot to throw a bunch of stuff at you!
What I’ve learned with the MMM journey so far: Hedonic adaptation is very real. You get used to the luxury that you own and it’s hard to give it up. So for those reasons, I hesitate to ask you to throw it all away at once, less you get disinterested and go back to the spendypants lifestyle.
The car thing is hard for some people, because in North America cars are tied to your identity. You judge yourself and others based off the car that is driven. If you are big into outdoor sports, it feels really weird to own a 2005 Hyundai Accent. Not because of the utility that you actually get from it, but from the lifestyle appearance that it gives.
I’d be willing to be that I haul more gear, mountain bikes and construction equipment (and on more trails) in my 2009 Pontiac Vibe than your wife does in the Cherokee. It’s not one that I would bet my life on, but I use the heck out of that thing and it doesn’t complain one bit. If I were on fire roads all the time I’d want something with more ground clearance, but a Gr. Cherokee doesn’t really even have that much cabin space.
But this doesn’t really work if you feel like you’re sacrificing for it. I like to gamify it. I love showing up to Home Depot and fitting more stuff in my car than people throw in the backs of their F-150’s. I can fit 8’ boards in there with no passengers. It’s about the mindset change… and that takes time. First absorb it and as soon as you feel like it would be fun to downsize, that’s when you go for it! The trick is to think about all of the stuff that you gain by loosing the Jeep or Tesla (or both) and downsizing.
My maintenance is absurdly low. I paid $8K cash five years ago for this thing. It looks OK and would be fine to valet park, but it’s no princess which means that I don’t mind if it gets dinged up a little bit. It’s a great little tool and all of the important bits are humming along quite well. But that’s fun for me. My wife likes the aftermarket heated seats that I put in.
And my car, an econo box from 2009, has a 110V electric socket in it. That’s insane to me. It really is a driving living room.
TL;DR- if you are in the right mindset, you will genuinely be happier getting rid of the rolling depreciation luxury living rooms and downsize and start commuting by bike. Do it on your own terms and like others said, don’t sell now just to buy again this summer. I personally would love to haul bikes around on a Model 3. Take it in steps one at a time and enjoy the journey. In a few years you may be surprised at how far you've come by having fun saving money.