Sometimes. All I can speak about is my personal experiences with a handful of enterprise customers and the times we moved things to the cloud. Communication is always an issue, we find that instead of spending time in house developing, deploying, administering, etc... we spend that same amount of time either one the phone or writing emails and documentation on what we need or what is wrong or what we need done.

We also find that the what the cloud team finds as a sufficient level of quality or service often does not match what we require or expect. And fixing that is a major PITA because it comes down to culture, and suddenly you are not dealing with your company's culture but a 'cloud' culture.

And on top of all that there is the issue of who controls your data. Is it secure? is it safe? What's your uptime, downtime, maintenance? Often we get promised good things (sales people are good at what they do), but it rarely works out as such.

The answer to this is find another cloud provider, but I dont want to spend months RFI, RFP, migration, integration, etc....again because the first cloud people were terrible. It's often just better in the long term to do it yourself.

It's a pay me now or pay me later scenario and I'll live by the words if you want something done right, do it yourself, especially for enterprise.