@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.
