The cancel is an easy one. I collect stamps as well, and this sort of thing is pretty common.
Chicago was a very busy post office. Some offices back then were open late, and on sundays and holidays. Cancelling would be the first thing done and they tried to do it as close to the time of a card or letters arrival at the post office. In a small town it was usually cancelled immediately at the counter.
In a busy office like Chicago the mail would have been processed through a cancelling machine in batches. The machine used here was hand loaded, unlike the ones of today that do their own arranging of the mail. On the first pass through the machine during the 9:00 hour the cancel mised the stamp. The postcard was probably between a couple letters and didn't get lined up correctly.
The guy sorting the mail by destination would have noticed this and held the card out to be recancelled. They were very conscious of stamps potentially being reused.
The recancelling stack would ahve been collected and brought to the canceller again, and recancelled. In this case during the 10:00 hour.
The 8 in the cancel is the number of the machine, Chicago had a lot of cancelling machines, probably more than 20.
Steve B
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