IMO i think that the toughest ride will be with the portuguese.They have 2 provinces separated one from the other, and the moorish empire breading on their neck. Challenging indeed. The second i think will be the scotish.Stranded on the north side of the map, next to the more powerful english, and not that many resources.Number 3 on this top, well... tough, but i think that the milanese are taking the bronze medal. To tiny and surrounded by powerful neighbors.