Binding in the AoL was rare--binding multiple times even more so. Remember, currency in the AoL was not money, but honor and respect--shame was the greatest punishment. In general, Binders were only reserved for those with compulsive or generally uncorrectable problems. The fact that Semirhage was given the option in the AoL of being Bound against her sadistic impulses versus Severed is an indication of how intense a punishment the Binder was.

With that in mind, I find it highly unlikely that many, if any, people were multiply-bound during the AoL (except during production and testing of the Binders). We've read first-person views of the mental effect the Oath Rod has--it's like wrapping a net around your head and tightening it. Indeed, this is psychologically what it's doing--binding and limiting your potential. The Ageless effect is probably a physical reflection of this mental binding--the more you do it, the more it wears and tears on your physical being--the tightness of the Oath affects your look (i.e. the Ageless look) and your lifespan.