"So what you mean is, that none of the women you've been dating "knew" at the time of the first 1-3 dates? You told them about it, when things became kind of serious?"

Yes that is basically the best way to handle it. The best rules are (in this order) #1 Don't wait TOO long, and #2 Don't let her find out on her own before you mention it.

Most guys who have their act together don't really have many, if any, bad stories about women not dealing with it.

Not sure if the whole full cap vs. topper thing changes the equation at all.