One more complication is, lots of CCs dont even survive the one year mark. I seriously doubt the card issuers would put in required infrastructure to track the future purchases for this theoretical taxability issue.

Honestly, I dont know why only one poster has his TYPs 1099 all wrong per his claim, while there are several posters said Citi actually is accurate in separate the TYPs earned from banking and from CC side - and their 1099's largely match their expectation of what the value might be. (They know the ballpark figures of their TYPs from the banking side.) These folks also have TYPs from CC side that are classified as "bonus" such as the flight pt turned TYPs - but so far we have not had anyone reported their flight points turned TYPs are being reported on 1099's.