Hello Sailor Adam,
We would like to help you sort out the situation with your Surface device which cannot connect to an external monitor via mini DVI or wirelessly. To clarify, are you referring to Surface Book 2 or Surface Pro 5?
You can also check here to troubleshoot issues connecting the Surface device to the external monitor.
Or
Are you using docking station which is manufactured by Microsoft or comes from a third party store?
If you are using Microsoft docking station, you can download and run the Surface Dock Updater to ensure that your Surface Dock has the latest update. And lastly, you can also check here if your external monitor is compatible with your Surface device and Surface Dock.
Let us know if you need further assistance by replying to this thread. We'll get back to you as soon as we can. Thank you!
Regards.