Highway cruising, off roading mid sized SUV

A close friend of mine just bought a 2014 4Runner. He got the Limited, which he said feels much better on-road than the SR5 (which is what I tested and found quite roly poly back in 2010). The Limited does have a different suspension system. Few vehicles have a stronger reliability record. Which trim level did you test drive?

The 2014 Jeep Grand Cherokee should be fairly reliable if and when they sort out the electronics for the new infotainment interface. With the 2011, most problems were sorted out in time for the 2012. Avoidable past problem areas include the optional air suspension (a problem area in MANY vehicles) and panoramic sunroof (rattles). Most different with the diesel.

The Outback is getting redesigned for 2015. Cliche or not, it's worth a look.

There's also the Forester, which drives well. It's just nothing special to look at, inside or out. The turbo model is very quick, but the non-turbo engine might suit the basic character of the vehicle better.

I realize that you more-or-less ruled out all save the Forester in your post, but there aren't many choices among travel- and off-road-friendly SUVs that won't cost a mint to buy and/or maintain.

I own a Grand Cherokee (as my user name indicates) The sort of use you describe is how we use our 5.7 overland 4x4 GC and it has served us well to the current ~53,000 miles.
Our latest trip was ~2000 miles round trip, over 14 days. with approx 500-550 miles off road. moderate trails (hunting trails and numerous utility access road through east and central texas) We moved to the Jeep from a modified Land Rover Discovery (01) in late 2012. Interior and features are competitive between the Jeep and a newer Rover. Off road capability is as well (tho different solutions are employed by the 2 companies). People are quite unkind to the IFS/IRS platforms, but they can perform exceptionally well offroad with only 3 ,and yes even 2, tires in contact with the ground. it will take some adjustment if you are used to driving a solid axle 4x4.
You have a few really good options out there for this type of use. Reasonable on road manners, coupled with some off-road ability beyond an unpaved driveway or access road.The first few that come to mind: -Jeep Grand Cherokee The overland is great package but you really need to carefully weigh the benefits/risks of the QL-II air suspension system. For us it has been worth it, and allows you to cleanly fit 32" tires with zero modifications to the vehicle. Be advised there is some aftermarket support for the wk2, but it is extremely limited -Land Rover LR3 reliability is always said to be an issue, but the last few years of the LR3 seem to hold there own fairly well. Major after market support for the vehicle, and there are a few options for coil spring conversion or 'johhnson rods' in order to lift the LR3. Range Rover also Toyota FJ or 4Runner are both very competent. But the 2 doors on the FJ were a deal breaker for us. We preferred a Tacoma 4 door with a camper sheel to the 4Runner. Michael is correct on the issues with earlier years of WK2 Grand Cherokee. The sunroof is nice, but is rattle prone and this is even more likely if you do get off the pavement, same with interior trim. The QL-II air suspension is a nice touch, but as with mercedes and land rover, it is failure prone. esp on the earlier models. Repeated issues both on the compressor and on leakey valves/connections. Warranty covereage has never been an issue for us, tho ability of the service tech to find the issue has.
I suggest the 5.7 or diesel, the larger brake package, and QD-2(4-lo, rear e-lsd). should be available in either limited, laredo or overland trim

We have sample sizes just above the minimum for one model year each of the LR3 and LR4. The latter has consistently been much more reliable, about average lately, and also performs and handles much better on the road. Still a tall, heavy vehicle, though. Similar to the 4Runner in this regard.

Like anything European, the LR4 will be more expensive to fix when it needs fixing.

I'm driving a 2014 Range Rover Sport this week. Better than a BMW X5 (and much better than a first-gen RRS) on-road, and highly capable off road. But also way over the budget cap.

Just talked to my friend with the 4Runner Limited, and he reminded me that it has a low range. It just doesn't have disconnectable stabilizer bars and crawl control, and you'll only need those for fairly extreme off-roading.

The tires with the 20s have a 60 aspect ratio, so there's still quite a bit of sidewall. The Trail might still be better for your needs, but I wouldn't quickly rule out the Limited.