The CVT and the boxer engine are major turn-offs for me, with the CVT being the biggest issue.
Stellantis dealers seem pretty desperate these days, and I wouldn't be surprised if they start throwing in perks like chauffeuring you around for the first two weeks after you buy a car. If you're in the market for a Jeep, the Grand Cherokee with the 8-speed ZF 8HP50 transmission and AWD is a solid choice. It's got a planetary differential in the transfer case which is a nice touch. Also, the Pentastar engine is reliable, especially if you swap out the standard oil filter housing for an aluminum one early on. Oh, and you can safely tow with it up to 7,500 lbs. It has the same power train they install in the RAM 1500 full size pickups.
If you're really into Subaru, that's totally fine too. Out of their lineup, I'd probably go with the Outback.
Ahh not so much on the Grand Cherokee....the V8s are gone (those could tow 7200 lbs) and were very hard to find even in the last 5 years, unless you bought the higher trim levels that also stuck you with the trouble prone air suspension and wrinkle prone leather dash cover. So most you will find are Pentastar V6s, with no low range on the transfer case and they are rated to tow about 6200 I think.
That's why I still have my '07 Grand Cherokee 5.7. I like it better than what they have been building the last 10 years or so.
We also have a '17 Forester (73,000 miles). In general it has been very good, problems we had, have all been covered under extended warrantee programs on certain parts:
AC condenser
shifter (could not remove key)
rear hatch struts
front control arm sway bar bushings
all this was covered free of charge no questions asked.
The CVT, I am still not used to, but the car performs much better than our first Subaru ('98 Outback) which had the same size engine and the 4 speed auto. That one was great up to about 110,000 miles then it had a whole passel of headaches:
head gaskets (blew at 109,000, fixed it, then blew again at 186,000)
wheel bearings
CV axles
sensors (anti knock sensor, speed sensor)
gas fill pipe rotted out and leaked gas on the driveway
But my better half likes Subarus so we got the '17 Forester lol.
For myself I'd like a BRZ.