Speaking of trade in value. The Subaru I just traded in was a 2015 Outback with 107,000 miles on it. Mid level options. I was given $9500.
If you are in a place with seasonal ice and/or snow I would go Outback; warm climates/Southwest maybe more the Jeep. I love my Sube but on long flat hot stretches of road the Cherokees I’ve driven have been way more comfortable.
Unless you’re absolutely married to the idea of the Jeep lifestyle and brand, you should go for the Subaru or walk everywhere. Jeep is to the automotive industry what Harley is to the motorcycle industry: image combined with grievous unreliability.
Spoken like someone whose knowledge of the subjects comes entirely from what he’s heard people say on the internet.
We had a 2003 Outback for 13 years, never had any major issues with it. We moved on to a newer Outback, and our neighbor’s son now drives our old one around. My neighbor said they had one $1000 repair last year, but otherwise it still runs great.
Another vote for Subaru, it’s likely to be more reliable.
Sounds like an abused Jeep owner making excuses for his preferred ride.
I have two Grand Cherokees, '97 and '09, 5.2L V8 and 4.7L V8 respectively. From that standpoint, I would question the V6, but your son probably wouldn’t miss that if he’s not doing a lot of hauling. Transmission-wise, there have been a few recalls on the WK, so definitely make sure those have been addressed if you go that route. Oh, and if the A/C compressor suddenly quits, get it into a shop quickly, because the system isn’t actually off even if you think you’ve turned it off, and the shaft will keep spinning and burn out the compressor, which (aside from costing a lot and making a huge mess under the hood) makes the interior smell horrible.
Regarding the climate, I’m not sure whether the Subaru or the Jeep would tolerate the road salt longer. (The original, plastic-clad Grand Cherokees (ZJs) were especially prone to rusting out along the rockers.) Both of my Grand Cherokees are excellent in crappy winter weather though. Having the appropriate tires helps a lot as well.
I have very little experience with Subarus, other than 1) they’re roomy and 2) they’re nice to ride in. They do seem to be very popular as winter vehicles in Maine.
Note my user name. Also note where I live. I have had a few Jeeps in my time. I have also had a few Subaru s as well.
First IMHO, the Jeep you are looking at is a Jeep in name only. It is no match for the older Willys Wagons, or the early Wagoneers. Nor is it a match for the Subaru in terms of either reliability, or creature comforts. Longevity of service is another area where the Subaru shines.
Keep in mind I am the guy that buys almost all of my rigs when they are at the end of their useful lives. It is cheaper that way. I am a fairly good mechanic & small things like head gaskets do not bother me too much.
Speaking of head gaskets, the Subaru 4 cylinder is the one that is noted for the head gasket issues. However, the six can have an issue as well if it has been run hard & put away wet. IE: If the PO did not allow the turbo to cool off after freeway use, &/or the maintenance has been neglected, they will fail.
If the head gasket fails & the repair shop does not pull the engine to repair it, it will likely fail again. I have bought quite a few Subaru s with a second or third failed head gasket. Every time the repair facility did an “in frame” repair. One cannot keep the cylinder block oil free while installing the head gasket if the engine is still in the car. Oil will damage the new head gasket’s seal with the cylinder block if the surfaces are not very, very clean. Oh I suppose if the rig was laid on it’s side it would work for the upper head. Let’s not be too silly here. None of my head gasket replacements have ever failed. I always pull the engine in a Subaru.
I have had at least 3 Subaru s go over 300K miles without any major issues. I cannot say that for any of my Jeeps.
IHTH, 48.
Subaru
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I had an '09 2.5i Outback. It was fun and an absolute beast in the snow. I did the head gasket thing at roughly 80k to the tune of $1,600.
I sold it earlier this year because I shoulda got the turbo or the 6, but I still miss it. Despite the head gasket issues, the Third Gen Outbacks were the Best Outbacks.
I got something like $5,500 at a Buick dealer as a trade in earlier this year with 110k on it.
Jeeps are cool, but they are about as reliable as a $2 watch (or whatever is the hallmark now for unreliability). Get on if you want to go off road a lot.
Subarus are as reliable as a Rolex. They are boring, however.
Thanks to everyone who contributed. In typical SDMB fashion, I took all the great advice and chucked it into the trash.
Kinda.
I passed on the Jeep GCL. But I also passed on the Subaru Outback. The former did seem to be plagued with reliability issues. The latter, while being surprisingly good to drive (for the type of vehicle), seemed to show a surprising amount of wear and tear compared to other vehicles of similar age and mileage. Granted, mine was a very small sample. But the wear of the interior materials: switches, seats, soft and hard surfaces - all seemed to show more wear than other comparable vehicles. It’s possible that the previous owner of these particular Subarus were just not very concerned with upkeep.
Anyway, at the end of the day, I plunked my money down on a 2006 Nissan Xterra 4x4 with 78K miles. Initially we considered the Toyota FJ but those have become quite expensive, even the high mileage vehicles, due to high demand. The Xterra is a similar vehicle but at a better price point and similar look and feel. Possibly not rated as high in reliability at the Toyota, but not in any real world sense that I found to be meaningful. No doubt you’ll set me straight and show me what a terrible mistake I’ve made. 
If you must do so, be kind.
And yes… it is not lost on me that I just bought a Datsun! 
It’s also possible there were some odometer shenanigans. Always good to pay attention to red flags like that.
Well, their brand is good. How Much Do Car Maintenance Costs Increase with Mileage? | YourMechanic Advice
Across their brand the estimated costs are 50% higher vs Toyota, but that could easily be due to variance. Nissan and Suburu appear to be similar.
Also the fact that yours was in poor condition goes a long way towards answering my question: if everyone knows the used suburus are great, why was this one around the same price as the used garage queen Jeep.