I'd suggest excluding your login from group policy firstly when you are able to login which should hopefully stop it getting stuck then add another test login and try to match the login you have been using in terms of group policies and run Resultant Set of Policies on it and see if you can find any problems with the printers it's trying to set.
Are you getting any errors in the event log regarding this?
Are you logging into the server via RDP/VNC or VMware console? If you're using RDP then check event viewer logs on your server as well since it's probably trying to map your client printer to the RDP session.