multiple remotes on a garage door opener with rolling code

After doing some research I think I now have a basc understanding of the rolling code technology used on garage doors. What I need clarification is the issue of multiple remotes. The way I understand it everytime the button is pressed the remote and the receiver create the next code to be used. If the remote is out of range and the button is pressed- that is ok since it has a look up table of 256 codes which can also be used. This way the remote and receiver are not out of sync. The second remote can also be used because of these 256 codes, so the second remote remains in sync even though the 1st remote has been used a few times. What happens in the situation when I use my remote for a few weeks - lets say 300 times and then we try to use the second remote? shouldn't it fail?

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