Been there, done that. Seriously considered it. Did test drive TRD Off Road (not the Premium one).
So, let's see.
First, why regular TRD Off Road and not Premium?
I'm ~6' tall. Premium comes with a moonroof. Inside 4Runner is noticeably smaller and the roof is lower. When they installed the moonroof, the roof becomes even lower. The way the seats are positioned, you can see where the roof liner comes down to accommodate the moonroof. If you tall, it doesn't feel good especially when sitting in the second row. More, if I move forward while sitting on the second row, I hit the roof liner with my head.
Gas mileage. With stock tires one can get promised gas mileage, 17/20. One better not to drive faster than ~70 mph as at 80 gas mileage drops to almost 15.
Suspension. I'm not sure how it is on the other trims, but on TRD Off Road it is way too soft. So the handling is way worse than the Passport/Pilot. I'd say replacing it is a must and not only for the lift. KDSS you ask? Not sure as I could not locate a single vehicle with it anywhere close to MA.
Acceleration. Anemic. It is built for off roading and anemic gas pedal works great for it. Getting it as a daily driver, might lead to frustration.
Interior. Way outdated. Head unit is from the past. Can be replaced with aftermarket units. Cost is probably $1000-$1200 before installation. Also, SofTex seats in Premium - really? Not for me. I better live with cloth seats.
Controls on steering wheel. I guess I used to Honda. On 4Runner I found them not in place.
So, as I was looking for a vehicle mostly as a daily driver, the list of cons was too long and I decided that I can live with that if I can get it at around $32k-$33k. Than suspension and head unit upgrades would move it to a level of Passport Touring (invoice).
Well, the best offers I've got for TRD Off Road was ~35.4k for 2018 and 35.7 for 2019.
It might be all reasonable and make more sense if you live in the area with more off-road opportunities. In MA to me it didn't make sense.