@Phaedrux I uploaded the attached wifi server version and was able to upload a file afterwards. However, I was able to upload the .bin via DWC (which has been failing previously) so I may just be in one of the periods where I am able to upload. I will monitor over the next day or so and see if this wifi server version actually resolves the issues or not. I did not the load times are significantly longer, though that may be expected.
@gloomyandy I was about to reply saying nothing had changed, outside connecting an accelerometer well after the issues started, but I did double check and it appears my Unifi APs firmware was updated the day the issue started. I hope that isn't a cause of the issue as I really don't like the idea of rolling back networking firmware (which included security updates). In the meantime, I'm going to try connecting my board to my phones hotspot as the only way I have to eliminate my network from the equation.
I will update tomorrow with my findings on both of these items. Thanks for the help so far!