Thanks to all for your help so far. I have access to the St. Louis, MO city directories and have most of the directory information for when the three people were in business & where. If I can find the 1866 auction catalog reference to the Traebing token I can make a better case for when the tokens were made & used.

The earliest auction catalog mention is the 1876 Centennial auction catalog (can be found on the Newman Numismatic Portal), but that only tells me that the tokens were issued pre-1876. A firm 1866 date would give me a nexus for establishing a better idea of when they were first used.

I believe they are Civil War era tokens (as opposed to Civil War tokens), but the 1866 catalog that Steve Tanenbaum mentioned to me is the key.

I haven't been able to find an official estimate, but think 800 is a reasonable number. According to the Federal Reserve, the average dollar bill lasts about 7.9 years, so if you assume it gets used once every one or two days, that gets you in the ballpark.

Mind you, a typical dollar bill will often be collected by cash-in-transit companies and cycled through machines that sort for fitness. If it is is still in good condition, it'll be recirculated. But if it has a marking on it, the machine may decide to classify it as no longer fit, and thus ready for destruction. In which case it won't see 800 hands.

This earlier E-Sylum article seems to say it all, definitely coming down on the side of inclusiveness, not delicacy.