Is it really so difficult to put on a sheitel properly?
Good question, no answer.
But I guess I can ask similar questions on plenty other minhagim or grdorim. That's what it is and I have no problem with it as long as its not forced.
And if that's the real issue so get a short haircut so there's not even a chance of stray hairs coming out of a sheitel, why shaven?
They do get boys haircut (at least my wife). Don't know who misinformed you all.