Thinking of these options

The Honda Pilot for those years have some suspension and brake issues. They are fairly reliable as the redesign was in 2009 so most of the transmission issues those years you mention were worked out.

Jeep won't last as long as the other two. However, the years you picked on that Cherokee they are okay although the 2016 are starting to show some transmission issues. So you take your chances as far as reliablity goes.

The Subaru has oil burning issues but if you watch the oil level they are otherwise reliable. The 2015 was redesign year so I would avoid that one year of the years you listed. It does tend to have more issues than the 2014 and 2016-2017 model years.

There is always Toyota Highlander and 4Runner as well but you did not mention them.

The 2014-2015 Cherokees were horrible cars. The 2016-2018 are better, but why go with an initially unreliable car? Transmission problems are still common. I know reliable Toyotas are expensive when used, but Hyundais are not expensive and are still reliable. I have never seen so many transmission failures under 20k miles as the Cherokee has.

For the Pilot, I would get a 2013 or newer one. The 2009-2012 had excessive oil consumption. The only ones with transmission issues were 2003-2005 and the new jerky 9-speed.

AcuraT said what I would have said with the Outback. I'd get the V6 if you will be towing often because the 4 cylinder is already slow without cargo. 2015s had a lot of cracked (cheaply built) windshields, a terrible repair if your insurance doesn't cover it because it is around $1000 and isn't covered under warranty. This happened with my 2016 Prius, but my insurance covered it. Safety cameras "need" to be recalibrated

I know it is pretty old, but the 2012 Toyota RAV4 offered a 3.5L V6 and had a 0-60 time of 6.5 seconds, which is great for drag racing and towing. They rode smoothly and with the tow package can tow 3500 lbs. That's a lot for a compact SUV. This is the most reliable car on my list.

The Highlander is also good, but not as fast as the RAV4 V6 and might be a waste of interior space. Very reliable, more than the Pilot and on par with the RAV4.

The Jeep Cherokee won all sorts of awards for design its 1st year. Yet test drives suggest that its interior is not very spacious given exterior size and the transmission is not well refined. Cherokees are not reknown for their reliablity. That said Consumer Reports gives the 2016 a 3/5 reliabiity rating - not too shabby. More troubling is the fact that CR gives the same rig a 2/5 consumer satisfaction rating -- pretty shabby!

A small current generation 2.5i Outbacks do have their oil burning & gasket issues. But overall are a vastly better car than the Jeep. I have towed a 2000 lb boat quite a bit with my 2010 & 2015 2.5i Outbacks and found it adequate even for mountain passes. My only concern was that it seemed a bit heavy for the brakes; thankfully I never had to do an emergency stop. If your towing to E Coast would be primarily freeway, your loaded trailer weight is under 1,500 lbs & vehicle isn't heavily loaded; and you satisfied to travel at 70 mph,

I think the 2.5i will do the job for you. If your load is heavier or you would just prefer the extra power, the 3.6R would be preferable. Brakes are the same regardless of engine so no tailgating!

You could get a new 2018 2.5i or even the 3.6L H6 Outback Limited with most bells & whistles for your $38,000. That's how I would go!

Overall, I pretty much agree w ElectroFuel & AcuraT with this exception: It is rather commonly held that that windshield replacement on Subarus requires a recallibration of the Eyesight system. I had my windshield replaced (under warranty and didn't need Eyesight recaibration. The Eyesight performs flawlessly both before & after.

Safelite said I needed a recalibration, but everything worked the same before I recalibrated it with the new windshield. Toyota said they would recalibrate it for free with my oil change, so there wasn't a reason not to.