Hi there,
We have a problem where we are moving files out of a folder into the trash and then attempting to put files of the same name back into the folder. However, because the remap manager has stored the paths and names of those files, the system registers that the file already exists and refuses to upload the new same name version of the file.
Now, if you manually use the remap manager and delete references to the file of that name, you can upload a file with the same name.
A: Is that a bad thing to do?
B: How would you set it up so that the remap manager doesn't hold that url - I see there is an expiry value for the remapped path but have no idea how one would set it, so how do you set the expiry date for a remapped URL? Can it be set up automatically for certain assets?
The manual tells me what it is and what it does but not how to do it.
Thank you 
I can provide a little info on B.
You can't stop Remap manager from storing old urls automatically, and only manually entered URLs can be given an expiry time (automatic ones will exist until removed).
Theoretically, remap manager shouldn't be the problem. You should be able to trash files and upload ones with the same name without having to clear the urls from remap manager, it will overwrite them.
Can you tell us what version you are using? This may have to be reported as a bug.