This is based on my experience owning a 2008 JKU for the past 12+ years and renting a 2018 Tacoma TRD extended cab for a day. I've always liked Jeeps and small/mid sized Toyota pickups. When it came to buying my vehicle, it had to be a family hauler and I really didn't have much use for a pickup bed. I looked at the Toyotas but the JKU was fairly new back then and I just liked the look better. It had 4 doors and plenty of cargo space. With the rear seats folded down it can haul a lot of stuff. And I loved the fact that the top can be removed. The thing is that before this Jeep, my vehicles had been mostly Hondas. I was leery of owning a Jeep. But reality is that my JKU has been more reliable than any of the Honda Accords I've owned. It's massively capable off-road and can take a lot of abuse without breaking. I've done trails easy to moderately difficult and not broken anything on it (bent some plate underneath and the exhaust though).
The 2018 TRD extended cab was fun to compare. It also had 4 doors and seemed comfortable enough. On highway it was just a little bit smoother riding (because of the IFS) than my JKU (I've put bigger tires on my Jeep). There was definitely less wind noise which was nice. However, I hated the completely numb steering on the Tacoma. The Jeep doesn't exactly have sharp and communicative steering like my sports car but it's better than the Tacoma by a lot. The Tacoma engine/transmission does have a little bit better power than the old 3.8L in the JKU.
When I decide to upgrade from my JKU, I'll likely look at a Jeep JLU or maybe even a little more upstream at the Toyota Landcruiser. After the Tacoma rental, I really don't have any desire to own one.