There are some things we've encountered that should have been relatively basic but turned out to be a nightmare. One is configuring a VM to have a public, static IP. I currently have a Windows VM running that somehow has no fewer than 3 different static IP's, depending on where you look. Yes, we followed the directions and had our dev ops guy give it a try.

Second, we deal with some third party vendors who require us to white list our IP's. We ended up having to config a VPN through Digital Ocean because even our dev ops guy and our IT guy together couldn't figure out how to route our traffic.