Does running an older Windows system restore point wipe out more recent ones?

Solution 1:

Old restore points are only automatically deleted and replaced by new restore points if the drive is out of space. There is no other reason for deleting restore points.

The answer is then that newer restore points will stay even if you have rolled back to an older one, and I have done this in the past. You should just be careful not to run out of the percentage of disk space allocated to restore points while doing that.

Note that although the restore algorithm is pretty good, you might encounter unwanted artifacts while going back and forth between restore points. It's best to only rollback if you absolutely need to.