Is there a way to make updates in ArcMap sync with AutoCAD (or at least make that update process quicker?)

You can use a ChangeDetector to get the changes from two datasets and you can write these changes to Autocad. Here is a handy link for working with Autocad: https://knowledge.safe.com/articles/22968/getting-started-with-autocad.html

Hi @mattjelbert,

If you are new to FME it would be good to have a look at some of our tutorials that explain a little bit more about how the software works: The Getting Started with FME Desktop series is a 4 part tutorial covering some of the basics with video explanations as well.

FME Desktop can handle both .dwg and .mxd formats (note .mxd is only supported on Windows OS) and because of this it is likely that you should be able to set up a workspace that can look for updates (@stalknecht suggested one example of how to do this) and then transform data accordingly. If you want to automate this process further then you could look into our FME Server product which provides a level of automation for these workspaces - based on a schedule, or perhaps using Publications to monitoring a directory or email etc and then setting a job to run your workspace based on these events.

If you would like to trial FME Desktop you can make a request here: https://www.safe.com/fme/fme-desktop/trial-download/