If it's your wife's DD, then she needs to make the call. We had an Outback years ago that was my wife's, but when she had a baby I "gave" her my 4Runner and I used the Subby as a commuter. She hated the 4Runner - too "truck like" - and it was sold 6 months later. I think some people (women)...
The 2005 V8 also got a boost in power numbers, so if you are towing there is another compelling reason to look at 2005+. That V8 is the same 4.7 platform that the 100 series, Tundra and Sequoia run, and it's reliability is excellent. The 4.0 V6 is a nice motor, but if towing is a priority...