I've noticed concurrent ORD sessions can only be run if ORD is loaded using "Open With" for files (vs using desktop icons) - is this intentional? Microstation Connect seems to have the same problem.
Following up on that, any second running session results in this error on startup and an immediate shutdown of the new instance of ORD - I think this is related to my other post regarding Geometry Export Crashes though:
OpenRoads Designer 2021 R1 (10.10) | Microstation CE Update 16.2 | ProjectWise CE 3.4
Try this ... right-click on the ORD icon and go to Properties. Once there, go to the Compatibility tab and enable "run as administrator".
Apply the changes and then try running multiple sessions again. Let me know what happens.