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From memory wp_upload_dir() is only called once, so it probably would work, although of course you would have to be careful not to over write with new releases.
I probably could put in a WP-CONFIG parameter to override the directories.
But I do have some concern, ” The RentPro information gets pushed to a Rightmove directory in the root of our client’s site.” if you use this here for anything else, as my plugin will move the file into ‘processed’. I also would need to know if the root of the website is actually visible (i.e. public_html) because processed directory needs to be visible to the web to allow All Import to work.
The plugin can’t work across external servers, so the files will need to be moved.
It sounds like you need a little bit of sys admin support. If you have shell access to your server(s) and assuming Linux, as I believe rsync could be used pretty easily ( see http://linux.die.net/man/1/rsync ) to get teh files to the right place from either the local or remote machine.
Let me know your thoughts.