@BillPfahnl, we have a similar setup with Office365, Jive, GoToAssist/Meeting, Evernote, Dropbox, VPN, and Remote desktop. We haven't moved to Azure as yet.
My challenge has more to do with each employee's home network. I spend an inordinate amount of time troubleshooting issues with personal routers, internet providers, bandwidth issues, VOIP QOS, inadequate wifi coverage, etc. Many times, folks working from home are used to consumer level requirements for web surfing. That's all well and good until you try to implement a VOIP service across a wifi environment where the router is in the basement and the office with PC with the softphone is on the second story of the house. Can't pull a wire because it might mess up the custom, hand painted wall paper in the office. Yikes!