So I've seen the Wiki showing how to use the Auto Upgrade feature in RouterOS but it points to a router. Can I have it point to theDude and drop firmware in the dude or a windows server and have it check that in order to update the firmware. If someone could show me an example of how to do this that would be amazing!

Bump.

So if this cannot be answered what are some ways I can have all of my CPE's upgrade automatically to the most stable version of RouterOS?

if you have theDude monitoring your network you can create router groups and then upgrade whole group using theDude

I don't have every client on the dude. This would be excessive. I only have a few of the best signaled cpe's. Thanks for the suggestion but I'd really like to setup RouterBoards to check for an update somewhere on my network and then update if applicable. Any other options?