After several of work I found the solution to this issue.
It was as simple as creating a user called "portaluser" (the same as my app pool identity user) in ASSETSSERVER.
This is counter-intuitive: I explicitly told IIS7 to connect to ASSETSERVER as the assetsuser server, but it was still using portaluser to check for the existence of web.config (and monitor for changes).
Having seen that, I decided to use the same account to run the app pool and to connect to the remote virtual directory. I just used 'assetsuser' instead of 'portaluser'
Hope this helps