I can't give a complete answer (don't work for Adobe) but have you looked at Teams?
-assign a new team member http://forums.adobe.com/thread/1460939?tstart=0 may help
-Team Installer http://forums.adobe.com/thread/1363686?tstart=0
Yes, I've looked at teams but its will cost almost double the cost to manage the licenses that way! I'm guessing I will need separate ID's. Just curious if anyone else is managing multiple license with just the one ID.
I don't think that is possible... as far as I know, one ID only allows 2 computers
Cloud License allows 2 activations http://www.adobe.com/legal/licenses-terms.html
-Install on a 2nd computer http://forums.adobe.com/thread/1452292?tstart=0
-Windows or Mac does not matter... 2 on the same operating system, or 1 on each