I wouldn't hesitate to get an older AT. Not just because of their reliablity (it's a Honda blah blah blah), but because of their superior quality to the later ones.
When the Yamaha Tenere big monster thing came out a lot cheaper, Honda redesigned the AT taking off lots of little bits and pieces in order to save money, remarketing the bike at a price more like the Yamaha.
There is a higher ground clearance on the older ones too: they are, I think it is fair to say, closer to the trail/off-road idea that the XL series began with.
Gradual "improvements" have lead away from this towards a more road oriented bike. The same is true of the Transalp.
Not that later ATs aren't good ( they have a bit more power I believe), but for overlanding, I think that the older ones edge it.
Around the world 2000-2004, on a 1993 Honda Transalp