It is not possible to connect to a second Drive on Windows. When you try to do this, an error occurs in the AD log and a general failure message is shown to the user.
See also the attached screenshot. On Mac OSX, it is possible to connect to multiple drives without errors.
Tested and reproducible with with
How to reproduce
Error in the AD log
2012/04/23 12:00:32,343 [ConnectionHandler-Adobe Drive.exe-2796] ERROR MountService - osIntegration.mount() failed
com.adobe.drive.data.model.DriveException: the server with uuid elvis_server_192.168.72.87_8080 could not be mounted
at com.adobe.drive.internal.biz.filesystem.mount.OperatingSystemIntegrationWin.mount(OperatingSystemIntegrationWin.java:109)
at com.adobe.drive.internal.biz.filesystem.mount.MountService.internalMount(MountService.java:144)
at com.adobe.drive.internal.biz.filesystem.mount.MountService.mount(MountService.java:102)
at com.adobe.drive.ui.ncomm.handler.MountServerHandler.mountServer(MountServerHandler.java:274)
at com.adobe.drive.ui.ncomm.handler.AddServerHandler.handle(AddServerHandler.java:136)
at com.adobe.csi.internal.ncomm.InvokeHandler.handle(InvokeHandler.java:88)
at com.adobe.csi.internal.ncomm.NCommDelegate.execute(NCommDelegate.java:107)
at com.adobe.versioncue.internal.nativecomm.host.Host.execute(Host.java:200)
at com.adobe.versioncue.internal.nativecomm.host.ConnectionHandler.handleRequest(ConnectionHandler.java:162)
at com.adobe.versioncue.internal.nativecomm.host.ConnectionHandler.run(ConnectionHandler.java:81)
at java.lang.Thread.run(Unknown Source)
2012/04/23 12:00:32,368 [ConnectionHandler-Adobe Drive.exe-2796] ERROR AddServerHandler - Adding server failed
com.adobe.drive.data.model.DriveException: the server with uuid elvis_server_192.168.72.87_8080 could not be mounted
at com.adobe.drive.internal.biz.filesystem.mount.OperatingSystemIntegrationWin.mount(OperatingSystemIntegrationWin.java:109)
at com.adobe.drive.internal.biz.filesystem.mount.MountService.internalMount(MountService.java:144)
at com.adobe.drive.internal.biz.filesystem.mount.MountService.mount(MountService.java:102)
at com.adobe.drive.ui.ncomm.handler.MountServerHandler.mountServer(MountServerHandler.java:274)
at com.adobe.drive.ui.ncomm.handler.AddServerHandler.handle(AddServerHandler.java:136)
at com.adobe.csi.internal.ncomm.InvokeHandler.handle(InvokeHandler.java:88)
at com.adobe.csi.internal.ncomm.NCommDelegate.execute(NCommDelegate.java:107)
at com.adobe.versioncue.internal.nativecomm.host.Host.execute(Host.java:200)
at com.adobe.versioncue.internal.nativecomm.host.ConnectionHandler.handleRequest(ConnectionHandler.java:162)
at com.adobe.versioncue.internal.nativecomm.host.ConnectionHandler.run(ConnectionHandler.java:81)
at java.lang.Thread.run(Unknown Source)
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