Effects on the canon: Martin Luther wanted to drop the the book of Revelation (along with a few others) from the Protestant canon, but was ultimately unsuccessful. But this had more to do with conflicts with certain aspects of his theology than being inaccurate about the timing of the end times. Because the Bible itself is cagey about the timing of that ("But about that day or hour no one knows, not even the angels in heaven, nor the Son, but only the Father." - Matt. 24:36). So when various groups were wrong about timing, other people had only to point back to this passage and pronounce the first group mistaken about timing. So, constantly expecting the imminent return of Christ while thinking the last generation was wrong about believing just that is probably as much a traditional feature of Christianity as celebrating Easter the first Sunday after the first full moon of the vernal equinox--i.e. mostly applicable but some people/groups differ.

There were some groups in the earlier church condemned as heretical after making incorrect statements about the return of Christ. Montanus (100s CE), for example, prophesied that Christ would return to the town of Pepuza in Asia Minor and set up New Jerusalem (which didn't happen), but he also prophesied in a way (ecstatic and in a more pagan style) that the Church of the day didn't like.

While this is more a question of Biblical scholarship than history, there should probably be a distinction made between the "end times" and the triumphant return of Christ, as there is plenty of reason to believe that much in, for example, Revelation refers to the early Roman persecutions of the church (in highly symbolic terms, of course, so rather than God-Emperor you have a beast with 7 horns demanding to be worshiped) and that other prophecies refer to the destruction of Jerusalem and the Temple and so forth. What's more the prophecies are still vague and symbolic enough to be read as applicable to any time (as in, which times in history do not have wars and famines and epidemics somewhere?) so people can still look at the prophecies through a contemporary lens.