Depends on your personal preferences. Pilots have become more sophisticated and feature-laden with each generation. Gas mileage is better on the newer ones. Styling has changed. DIY maintenance has gotten more difficult as complexity has increased.
There are many discussions i the forum about which generation is best. There's no consensus - everyone's criteria are different. Reading a few of those threads will give you more useful information that the answers you'll get here.
Personally, with what you've stated here, an '06 - '09 Mercedes wagon would be tough to beat, but I use my '03 Pilot for cross country travel and its pretty darn good.