Tire width for a daily overland rig (JGC WK2)

Adding a 2.5" OME suspension lift to the 2017 Jeep Grand Cherokee Limited I picked up to turn into my overland rig named "Trail Dragon". However, this is also a daily driver.

Because I've run them in the past and loved them, I'm going with Toyo Open Country M/T: Off-Road Tires With Maximum Traction | Open Country M/T

I've already researched and debated the 18" vs 20" rim size, and decided to start with 20's. If you're curious why we made that decision for Trail Dragon, let me know, and I can start a new thread. In this thread, I wanted to discuss tire width specifically.

I was talking to my tire & wheel guy, and when I mentioned going with 295/55R20 on 20x8.5 he replied that it's a "very wide tire, and I worry about onroad handling. When they get that wide, there's a lot of tread squirm and they tend to make the Jeep very "darty" feeling. Is there one that's more narrow that suits you?"

The 295/55 calculates to roughly 32.8" tall/11.6" wide. The only other size in the lineup that seems like a good fit is 275/55. That brings the tire to roughly 31.9" tall/10.8" wide.

Because this is a daily driver that will see quite a bit of on-road miles in addition to going off-road, what are your thoughts here?

 

Since I already did it and I'm me, I'd buy a tire more suited to the 'quite a bit of on-road' use (= hiway) miles.. How about this one?
https://www.tirebuyer.com/tires/size/295-50-20
It's as tall as you want and probably safer on the road than a more-off-road tread type.. FWIW, I put 259/45-20s on my 'new' 2015 GC.
https://www.jeeps.net/threads/new-2...-20-on-15-grandokee-overland.4924/#post-37485
These obviously are much-more hiway tires than what you're considering, but it makes no sense to me to compromise hiway performance for what might be 2% off-road driving..

But we're all different and get to make our own choices.