1) Sure - but if you have any problems, you risk not being able to get support from TAC if it's not on the list..
2) I wouldn't want to guess, or predict.
CWMS takes a lot of hardware and you will most likely be running dedicated nodes for it, so running a slightly older version of VMware probably won't be too much of an issue. You can still add 5.1 to a 5.5 vCenter etc etc.
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ESXi 5.5 will be supported in Cisco WebEx Meetings Server 2.5 which is scheduled for release some time in September. You can monitor cisco.com and when the upgrade file becomes available, then you will be able to order full CWMS 2.5 OVA installation file via Product Upgrade Tool.
We are expecting it any day now. We didn't get a firm date yet. As for the enhancement you've specified, it is still in Assigned state and not Resolved state. I believe portions of the enhancement might be coming with 2.5, but I am not 100% sure about audio portion of the meeting being password protected. We'll know for sure once the product is released and all the documentation is available.
SIP traces provide key information in troubleshooting SIP Trunks, SIP
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