Support thought that it was a Root Certificate issue but their own links given to support didn't work to the certs they were told to try. The support rep said that they think it might be related to the latest SSU with windows 10, but it's impossible to just uninstall a SSU to test it..which all of my other machines have installed with no issue. Said they'd reach out if there we're any updates. That was 2 weeks ago.
@JLSantos I managed to figure out the issue myself. After uninstalling Citrix Workspace and rebooting, Logmein magically worked again. Even the inability to stop/restart the service was fixed.
I found it from looking into graphics drivers as the only thing different about this PC was that it had an old dedicated graphics card. I noticed in device manager that Citrix had it's own entry under display adapters listed as "citrix indirect display adapter". I remember Logmein used to use it's own mirror driver that showed up in Device Manager so I took a wild guess that it was interfering with whatever Logmein does to tap into graphics drivers. Perhaps it's seeing that device as a display out and tries to get a feed from it only to fail since it isn't a real display device. This isn't a solution because I still need Citrix Workspace but this should point Logmein in the right direction. Going to reinstall Citrix Workspace and see if I can replicate it.
Update: Reinstalling Citrix workspace didn't bring back the issue. But it also didn't install the "citrix indirect display adapter" that I saw earlier. Worth noting that I had manually uninstalled that driver within Device Manager before removing Citrix Workspace so that driver specifically might be the cause of the issue.
Update 2: Seems to be related to Citrix Screen Casting which is part of Citrix Workspace.
Thank you @slimjim1 !!! I just uninstalled Citrix Workspace and am now able to connect via LogMeIn! Thank you so much for letting us know what worked for you since LogMeIn themselves stopped updating us. If anything changes on my end, I will post in the thread.
Update: I reinstalled Citrix Workspace and am still able to connect via LogMeIn