- '06 Escape, 56K miles
- '05 Passat wagon, 65K miles
- '04 Outback Legacy, 80K miles

Personally, I would knock out that Passat right away. FWD vs AWD, expensive repairs, and reliability is iffy. The only way I would consider one is if it's diesel and stick (which seems to be the best combo for Passats/Jettas).

That leaves the Outback and the Escape.

First, to quell your fears about rollovers, the Escape is naturally much better than an Explorer when it comes to rollovers. Reason being, is that the Explorer is a body-on-frame suv, the Escape is a uni-body. Body on frame vehicles tend to have a higher center of gravity, making rollovers somewhat easier. With that said, newer vehicles have stability control, traction control, better tires, ect; which reduces rollover likelihood greatly. I wouldn't worry about it.

As far as which I would go with between those two, it's a bit tougher. Judging by the age and mileage the Escape is probably going to be in better shape. If that's the case, than that's what I would go with.

On a side note, one thing I don't like about Subarus is that, for many of their engines the recommended or required minimum octane fuel is 91 (premium). While they will run on regular (with reduced timing and power), I prefer to use the fuel that the manufacturer recommends. That means that, in some cases, you would end up paying more for fuel than you would have if you went with a vehicle that gets worse mileage, but is designed to run on regular.

Edit:

Just out of curiosity, I started looking at the gas mileage between the two.

Outback: 18/22 mpg (Premium Recommended)
Escape: 17/21 (Regular Recommended)

Doing the math, it would actually cost a little less to drive the Escape.