automate recovery of of known issues
use disable monitor (github) like code, or partner with that fellow to configure reliable placement of primary and tertiary displays. Such software could also probably be used to automate the recovery steps for the osx beta involving turning off all monitors and turning them back on... etc. Could be scripted and done without the user. At the least, check out the prj for quicker QA...
This can be done today, using standard OS interfaces. DisplayLink displays can be managed using OS APIs.
Any known issues or problems that can be detected or worked around are already done today.
This is not accurate. When I fire up my mac, every day, I have to ritually connect and disconnect monitors. Your own site lists in known issues that in beta mode that the main display should be moved to a non retina screen and then back... all of this is manually done through the GUI and OSX to my knowledge provides no automation for such tasks.
Also booting with my monitors is sometimes a crapshoot as to which will be recognized in what configuration, despite their having apparently unique identifiers using the CLI for DisableMonitor. Did you take a look at this project? I have no affiliation besides commenting on some issues and writing a plist to kill "phantom displays" on startup -- a persistent issue before I reinstalled OSX a second time... but it's super handy and provides hardware management tools that the average end user with more than just 2-3 monitors really wants to have available.
major typing lag there for a minute... compiling things plus typing... of of* = of.