I have owned Subarus (still own one) and Hondas. Not Jeep. I tend not to touch them because long term they don't generally last. Sure they are good for four years and 50,000 miles usually, but after that, watch out. They have electrical issues and powertrain issues. I tend to steer clear of them for that reason. You are seeing good deals on them for that very reason - most won't touch them. Don't be the one buying one unless you are okay selling the car after four or so years when the repairs start to mount.
Hondas are pretty good as long as you avoid a redesign year or the second year of production. They sometimes have issues with their transmissions the first couple of years they build a new one for a model. I have owned two Honda and between the two cars over 100,000 miles on both I went through two transmissions on one (was on my third) and went through one on the other (was on my second). So lesson learned for me - don't buy a Honda V6 in the first two years of production or you are nearly guaranteed pain on the transmission (TrueDelta and Consumer Reports also show this to be true as well).
Subaru's burn oil 10% of the time. My Legacy (the sedan version of the Outback you are considering, mine is a 2013) burns oil - about a quart every 2000 miles or so. That is "normal" for a Subaru so I just fill it all the time and pollute the environment. They are very reliable except for excessive oil consumption. You live with that, they will last you 200,000.