re: Beard guys... when does it get comfortable?

Depends entirely on how quickly yours grows, but the itchiness goes away at a certain length. From clean shaven, mine takes about 2-3 weeks to reach that point. I trim and maintain it, use shampoo and conditioner when I shower, and use beard oil for formal outings, though in well over a decade of having one it’s only itchy for that brief interval at the beginning.