Docker will not help you at all for this use case. A full Windows VM or a dual-boot environment like Boot Camp will probably be much better.
In theory you could run a Windows container on a Windows VM with it, but you can’t avoid the Windows VM. Also, interactive desktop applications just aren’t Docker’s strong suit, and I feel like Docker as a whole is still advanced-to-expert-level software. If this worked it’d be a rather unique environment that I’d guess a typical university help desk wouldn’t be able to deal with at all.