Some questions and ideas:
Was the salesman able to access the files before (so this is new behavior), or is this a new setup?
Are others able to access the files while using the VPN? (Others using Tunnelblick? Others using Windows?)
Can the salesman, when connected to the VPN, "ping" the file server using its IP address? ("ping" doesn't use the OS X standard DNS resolution, so results from "ping" by name can be misleading.)
Have the salesman put a check in both
"Route all IPv4 traffic through the VPN" on the "While Connected" tab of Tunnelblick's "Advanced" settings window.
and
"Check if the apparent public IP address changed after connecting" on the "Connecting & Disconnecting" tab of Tunnelblick's "Advanced" settings window.
The combination of the two checks will let Tunnelblick make some additional tests which can reveal DNS problems.
The power outages could have caused crashes of equipment like routers which could affect getting into the internal network from outside, even though from inside everything is OK.
Take a look at the salesman's Tunnelblick log (or better yet, the "diagnostic info" from the "Copy Diagnostic Info to Clipboard" button; see
Before You Post).