To each his own.
My 2002 Sport was a most excellent vehicle. I can assure you whoever end's up buying it (which may have already happened because I have yet to see it listed on the dealers website) is going to get a truck that was very well loved and maintained.
That being said, do I like my 2015 Trail more after a very short time. Hell yes.
That's not a knock on my old truck, but a manufacturer like Toyota does one thing very well - they improve what they build every year.
Read about the 2015 Trail KDSS suspension. It is some serious off-road technology and not even available on the TRD. Add the locking rear diff, crawl control and a boatload of other things and you have a pretty competent off-roader right out of the box.
Add the Entune audio/navigation system, 4 wheel disks, 120V outlet, etc.. and it's not even in the same league.
Loved my 3rd gen, but it's a different vehicle from a different time.