We have a (way over-)built 2015 and a nearly stock 2020 HE… both were purchased new. I love them both. I am pretty sure I would buy both again.
Having two is honestly pretty great. The old one is the dedicated camp, road warrior, offroad rig. Admittedly though it’s been getting too little use lately. The newer one is low mileage, maybe 20-25k.
My instinct is that the “we have two of the same car” thing often comes down to not wanting to move on from a platform once you love something but the reality is the Landcruiser will last a very long time. If I had left the original one alone it could just have been a 100-150K mile quasi daily driver.
My main regret, if you can even call it that, is going overboard on the first LC. Full metal front/rear bumpers with swing out, aux tank, snorkel, full rack, drawers, fridge, etc add real complexity day to day and aren’t that helpful for getting groceries or picking up passengers or making a school run…. Less is more with modifications for 95%+ of owners. The 2020 has OEM sized A/T tires, ARB onboard air under hood, sliders, and a rear goosegear cargo plate for securing gear. IMO it’s basically how the HE should have come from the factory. I will never, ever do the bumpers, full drawers, rack, etc on the HE…. YMMV
Now to address your other point, I bought a CPO Audi RS Etron GT at the end of last year. Depreciation after ~10K miles/2 years was over $100K

— happy to be the second owner rather than the first. And I can tell you that people are paying more than double what I paid for this EV on low mileage 200s on BaT. You can do that, but if you just need a car, can charge at home, have another car for roadtrips, etc then an used EV (with a warranty) can make a lot of sense.
The Audi drives unbelievably well. It’s infinitely better on a piece of paved road than a 200 Series, assuming you aren’t trying to drive across the country. I love the LC but it’s a dinosaur. The charmingly old steering and NA V8 give it a ton of character, but it’s good to keep track of what else is out there.
You know this already I’m sure but there’s something gratifying about having a competent, AWD, truly all-weather EV daily driver that can also do 0-60 in 3 seconds, and in this case for a fraction of what a late model 200 would cost. In my specific case, we can charge at home for next to no money, the service is much cheaper than any comparably performing ICE German car, and it’s just a pleasure to own.
Ultimately I would just think through it before spending big money on a 200 series (again) — but if you do, can’t go wrong with a LC/LX. They don’t build ‘em like they used, that’s for sure!