It is actually possible to win 5 Manager of the Year Awards in 3 Years! Yes, you can defy time!
How? I shall tell you. The Dutch Eredivisie is special. It has TWO, yes TWO, Manager of the Year Awards:
The Manager of the Year and The Managers' Manager of the Year.
However, there is no Manager of the Month award here but you can get this achievement in 3 seasons before spending a season / season and a half in a different league (not the Danish Premier Division either) to get 10 MotM awards. That will save you a whole season.
You cannot get these awards whilst on holiday but you can go on holiday during the season and still be awarded these awards if you return before the date. I played half the season and simmed the rest.
The date for the Dutch League around the 20th-30th of June. One season was awarded on the 24th and the other on the 26th. (I had an award for another league already).
NOTE: as with all awards in this game, you don't need to be #1. It counts if you come 1st, 2nd or 3rd.