General consensus so far looks like it's related to some third party application issues.
In my environment, eventlogs reported multiple user registry leaks.
My guess it has to do with the server being under load or some hardware (possibly disk?) related issues combined with the software combination and communications between tiers.
http://www.eversity.nl/blog/2012/08/a-timeout-30000-milliseconds-was-reached-while-waiting-for-a-transaction-response-from-the-name-of-service-service/
http://social.technet.microsoft.com/Forums/windowsserver/en-US/77a521a1-e3d5-4ab2-9c0f-be4a5498ce1c/windows-server-2008-sp2-stops-responding-as-multiple-services-timeout?forum=winserverTS
This thread has a bit more variations to the issue:
http://social.technet.microsoft.com/Forums/en-US/2c4b8121-da1c-4c11-b11d-2dff099ba245/windows-server-2008-r2-sp1-rds-hang-and-stop-responding-new-rdp-session-already-connected-session?forum=winserverTS
Official articles on how to change timeout. May not solve the root cause.
http://support.microsoft.com/kb/922918 (EventID: 7011)
http://social.technet.microsoft.com/wiki/contents/articles/1458.event-id-7011-basic-service-operations.aspx
Other (may be related)
http://technet.microsoft.com/en-us/library/cc756342%28v=ws.10%29.aspx (EventID: 7009)
Affecting VMtools:
http://ambitech.blogspot.sg/2013/01/esxi-5x-error-messages-in-windows-vm.html
Based on article comments, recommendation of not "updating OS patches + VMtools installation together" is not conclusive. (as in my environment, we patch first, then update tools)
Normal client OS with SSD:
http://www.bradymoritz.com/a-timeout-was-reached-30000-milliseconds-while-waiting-for-the
Seem to point to NOT disk issues. Hmmm...