For what it's worth, as one of the Rioters who was working on this maintenance I don't view it as entitlement at all. I know it sucks to have your servers down. Believe me, we don't want to do it unless we have to, and especially not during peak. This particular set of maintenances have been months in the planning with a lot of complex foundational work being setup in advance to make the actual maintenance windows as tight as possible.
As was mentioned in the short post that's been linked here in this thread, this specific maintenance is being done on a section of datacenter that happens to house some critical services for NA and OCE, that's why both were down at the same time.
This particular window was timed for the lowest point of impact for NA. Two weeks ago we did the same for OCE.
https://na.leagueoflegends.com/en-us/news/notices/league-of-legends-and-tft-server-maintenance-may-2020/