My wife would still be fine with the 4Runner. We are looking at some of the "shiny new gadget" vehicles (love that term) right now as well. We have never really used either 4Runner for what it is designed for. Just maybe some 4 wheeling in the snow- or a little off roading to get to a trail head. But that's it- well tow my race car as well. But the big difference to me in the used car market is I can buy a 4Runner with 60k miles on it and get north of 200k miles without even thinking about it. Not many SUVs will do that (IMHO). So I'm considering new for some of these SUVs.I'm not gonna claim to be super well-informed, but I have a strong 4Runner bias. It's sad that I can't say it's the best option for your needs at this point.
Yeah, the reliability and high resale value of the 4Runner can be a huge problem, especially if you don't have one anymore. I have a 2004 (got it in 2017), the current 2023 model is essentially the same thing, with a few dashboard upgrades.
I inherited a 2016 highlander in 2020, and had to choose which one to keep- kept the 4R, sold the Highlander disgustingly cheap during the depths of the C-19 lockdown. The highlander is a great ride, but more like a tall station wagon, not a real off-road SUV. Might be fine for most, most folks don't actually drive on nasty un-maintained 2-tracks and don't really need the capability of the 4Runner.
Jeep, VW, Hyundai, other brands all count on the "shiny new gadget" impulse buyers that forget about the value of long-term reliability when they are talking to the slick salesperson in the showroom. When I bought my 1999 4R in 2002 with 50k miles, a co-worker commented that I could have gotten a brand-new Chevy Blazer for the same price. Why yes, I certainly could have.... My '04 ain't too shiny anymore, Colorado's sun and hail have given it a beating. Not as severe as the financial beating of attempting to buy a new vehicle in the current economic environment.
So my search will continue- and I will look at many options. I do like your description of the Highlander- being a tall station wagon. My wife thinks it looks like a mini van. I disagree- the Honda Pilot looks like a mini van for sure.