I'm sorry James but we haven't been testing Mavericks for some time now. The latest release supports 10.10 onwards only.
If just the applications crash then it's best to raise the issue with Microsoft as they may have issues with virtual screens. If you are logged out from the Mac then it's likely an OS issue.
I'm using Office 2016 and Lync and I don't have DisplayLink-related crashes. Outlook 2016 does crash VERY frequently for me but regardless of the screens connected and I can restart it OK.
In any case it's going to be hard to receive support for Mavericks. Can't you go at least up to 10.11?
I have to say that the fourth 10.12.4 beta is the most compatible release since Mavericks came out (and broke quite a lot of functionality for us). Testing beta 5 now.
Cheers,
Carlo
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