I'm in a similar situation to Draconis Travis Immortalis, I'm a developer with two
external screens using this setup as a primary machine.
I had issues months ago where the system wouldn't properly wake from sleep which were resolved going through the update steps. It all worked beautifully for months.
Recently something changed. When I reconnect my surface to my dock or wake it from sleep the monitors are not recognized by the surface. I have to power cycle the dock to get it to re-detect the monitors and then it switches fine (driving the two external
monitors and switching the surface display off).
I'm running the latest firmware of the dock which used to work fine so I doubt its the dock. I suspect it is a recent update of windows which has caused the issue.
I am currently running update KB3213986 which was installed on Jan 13th. I suspect this was not the update as the issue has been around for at least a couple weeks.
The last update before that was KB3206632. This coincides with the issues and I suspect something in it caused the monitors connected to the dock to no longer be detected on resume from sleep.