Regarding the "Sign of the 8" token - I researched the advertisement provided by James Higby and it should be noted that the Wickersham store was also located in Wilmington,Ohio. The advertisements for the Robert and Robert M. Wickersham establishment start appearing in the Wilmington Clinton Republican in 1863.

I could not find an advertisement for William Preston at the "Sign of the 8" however the website Newspaperarchive.com has scanned the back issues of the Republican. I donot have a subscription to this archive but they provide a rough transcription of the newspaper contents. The July 31, 1863 edition contains the following:

So this would help to date the Preston token to having been minted before July, 1863. I tried to locate this business on South Street in Wilmington, Ohio but was not able tofind a directory that covered the needed years. The use of "Sign of" to mark a business enterprise has been in place for many years before the Civil War era. For instance in hisnew article in the December edition of the Journal of Early American Numismatics Gary Trudgen notes that Gerardus Duyckinck's Universal Store was located at the "Sign ofthe Looking Glass and Druggist Pot" in New York City. The "8" may have been a street number and/or the building likely had a large "8" sign in front that was distinctive and knownto all in the community.

Harold Levi writes from the North Georgia Mountains:

To read the earlier E-Sylum articles, see:
NUMISMATIC NUGGETS: DECEMBER 1, 2019 : "Sign Of The 8" Civil War Token(https://www.coinbooks.org/v22/esylum_v22n48a19.html)
NOTES FROM E-SYLUM READERS: DECEMBER 8, 2019 : Query: The Sign of the 8(https://www.coinbooks.org/v22/esylum_v22n49a10.html)