You don't think the medieval knight was more advanced than a Roman soldier?
No, I'm talking style not tech... And actually they weren't that much more advanced since they've now found out that Roman cataphracts (heavy cavalary) may in fact have had plate mail armor like medieval knights.
I don't really see it as a point that is being missed. I realize GL intended it to be "shinier and newer looking" but it just doesn't make sense. Time didn't start with the PT so you would still expect to see plenty of even older, well-used designs and tech then too. However, my grief also has to do with the tech rather than purely the aesthetics. There's nothing to indicate why technology, at least militarily, would regress leading up to the OT. Most of the gunships, fighters and walkers in the PT seemed far more capable than anything we saw in the huge civil war that rages 20 years later. Heck, the gunships even had mini-Death Star lasers! Why wouldn't that have been used more? I just don't think the Roman Empire/Dark Age analogy really applies here, at least not in my mind. There is no loss of knowledge happening here, apart from perhaps the Jedi teachings, and your average Dark Age knights and men- at- arms are still more advanced than Roman legionnaires.
The movies never indicated that Jango was paid for anything other than his DNA but as with any shadowy bureaucracy, one would assume the choice in trooper gear would come down to input from committees and corporations vying for contracts, not from an individual and his personal preferences.
Obviously, this all comes down to opinion but the bottom line is I think a sleeker, more modern aesthetic makes far more sense 30 years after the OT than 20 years before.
I don't think they looked more advanced at all. It just had flashier graphics than the OT. Just because the gun fired a fancy Death Star looking laser doesn't equal to it being better technology. The analogy had to do with loss of style and art, hence the Renaissance that followed. The Prequel tech was prettier and shinier and when the Empire took over things were utilitarian and bland looking. The movies might not have said it explicitly, but the novel did say that Jango helped train the clones. There were also no committees making the clones' vehicles and gear, so either the Sith designed everything or Jango helped design it. I really doubt they just gave someone a contract and told them to come up with whatever.