How bad are the first generation Touareg and Cayenne?

I am thinking about getting a new car to drive to work, but would also like to be able to do mild off pavement stuff sometimes, and it seems like these are capable of doing what I would want to do when they function correctly (basically driving on desert/forest service roads with more off road capability than a Subaru and better handling than a pickup truck). 

My thought is that a cheaper new car + a $5k VW/Porsche with the VR6 and steel springs to avoid the worst of the issues could potentially be a better idea than trying to do everything with one $40k SUV or pickup that's annoying to drive for all the things I could do with a normal car.  I know there are plenty of more reliable off road/soft road vehicles but these seem to be one of the best handling ones that also has low range available this cheaply so that's why I was curious.

Does anyone here have one? 

The VR6 ones are probably the most reliable motor wise.  Realize they're both old german cars and will suffer from OGC (Old German Car) syndrome.  You need to buy one from an owner who obsessively maintained it and has the records to prove it.  Even with that, expect some eye watering repair bills sometimes...

For some reason it seems the vw is a nightmare and the Porsche is a legitimately decent vehicle in terms of reliability.  It makes no sense to me given how much sharing took place on the platform.  The Touareg held the unlucky title of "World's most expensive vehicle to own cradle to grave".

My boss had a 2008 or 09 Touareg, I think with the V8.  He ditched it in 2011 or 2012.

It still ran, but he had spent a boatload of time and money with it at the dealer.

When you opened the rear hatch, water would run out through the interior panels... days after it rained.

Speaking of the hatch, he usually parked it in view of my office window, and I could see it open and (sometimes) close its own hatch randomly throughout the day.

A lot of the little electronic stuff just didn't work any more.

I remember (before current used car pricing took effect) seeing ten year old Cayennes on used car lots for under $10k.  There’s gotta be a reason for such a depreciation hit.

Nicest 6 Cylinder Outback you can find in your price range and add a lift kit and skid plate.

On the Porsche vs Touareg comparison, Porsche owners will have a tendency to spend more, and their rig will probably be in better shape.  I'm talking about examples that are presently still on the road, not the ones that have not driven in years. And as we are talking about old cars, the earliest T1/955 being now 17-18 years old, if an example is still on the road now, it makes sense to think that example was well cared for. Regarding the Touareg, I would not call it a nightmare. YMMV.  I had a 2004 (V8, air suspension, zenon lights, electric everything) and now have a 2008 (VR6 3.6, steel suspension, base model, halogen lights, OEM tow hitch, bought at 195K km, now at 235K km, paid $6K Can in 2015). I had the 2004 for 5 years and got rid of it due to electronic issues that were making me apprehensive of keeping it longer. Major ones were the QUESSY module that prevented the car to recognize the key or starting the car, a NAVI system that seemed to have been designed in the 90s and expensive to replace and an aging air suspension meaning airbag replacements. Please keep in mind this was before those replacement bags became much more affordable, as well as radio head units much more common. Regarding electronics, Germans in the early 2000 were not as good with electronics as they thought they were, and it showed in the Touareg. Anyhow, moving on a few years, after 3-4 years without my 2004,  I was still missing it so I purchased  a T2 (or a facelift one) , without the items I mentioned, a base 2008 with the VR6. And it has treated me well in the past 6 years I have owned it.  Is it the best? No. Does it do everything I ask it to? Yes. Did I spend a crazy amount on it? No. I did not make it a creampuff but used it as a truck, as a 2nd car, and it has done it well. If your intention is to go offroad, less is more, and base is better. There is something liberating about an old truck you won't mind scratching.  Ok, no bragging rights about the rear locker, but you can still do 99% of the same job. Whichever one you choose, it is a good time as they have gone down enough in value and the "overlanding" aftermarket for these is growing every week, making it probably a cheaper hobby then owning an ATV

Sounds like with low expectations, an AAA membership and a good pair of hiking boots a base Cayenne wouldn't be too awful?  I for sure don't want a V8 one. 

I already have a Subaru (although a 4 cylinder) but having something with low range would be nice.  I actually looked for a 6 cylinder Subaru before and couldn't find a good one.  They all leak oil so bad and the seats are shredded in all but the most expensive ones.