For example, I often hear that O365 licenses are a bliss compared to complexity of microsoft enterprise licensing, when even ms reps don't agree how much licenses you need.
To be fair, "the licensing isn't completely miserable like their other product" isn't exactly a selling point.
My two cents from what I've seen (note mainly see GSuite sie of things).. You can get much more productivity & actual collaboration with G Suite, dependent on a few factors.
One, there has to be total buy-in @ the executive level because you most likely need to completely re-think how work gets done across every function. Often, we do what we've been doing and don't see the full picture because of that existing perspective.
So that requires a legit G Suite partner to help execute change management as for O365 I imagine. It's not so much a risk unless you do it for the wrong reasons; They've done it enough times to have a proven migration formula. Saving licensing costs for example should be on the bottom of your considerations because that more or less evens out and becomes irrelevant.
Are there any "it may be down, but it is up quite often and saves us heaps of time and labor, totally worth the occasional outage" type experiences?
We're considering G Suite and O365 soon.