I am now assuming that you only have RF devices, correct?
If so there is one feasible option for this kind of setup:
> You can run OFFICE B's Checkmate in Disconnected Mode, you will have limited access to the data in OFFICE B, but you will be able to create text files with the data that can be e-mailed to OFFICE A and imported there.
However, I would recommend running from a centralized Server as this is the ideal setup and as long as Office B has internet access is very simple to do.
There are a couple of solutions for this:
1. We provide a free hosting solution called:
My Geotab. Using this you can connect from anywhere to the database. This also gives you some my.geotab only features.
2. You can host it yourself, all that SERVER in OFFICE A needs is an external IP and ports 80 and 443 open(which they normally are) and SQL with the database (which it should already have). Once this is done you can configure connection in two ways:
>Default: leave as is and users will need to run Checkmate from there pc's and connect to EXTERNALIP\Geotab/Geotab1 (\Geotab/Geotab1 could be different depending how it was initially setup)
> Checkmate Web Server: from the SERVER in OFFICE A enable Checkmate Web Server, a quick how to can be found
here. Then all that users would need to do is put in the IP address in an Internet Explorer browser, this will take them to a page with a Start Checkmate button.