A lot of Dyna owners would disagree with you. I was told by a well informed person, my brother in-law. Who owns a 2005 Fatboy with 1,600 miles on it. Sportsters are chick bikes.
I have a windshield on my Dyna Fatbob and I don't like eating bugs and getting rocks pelting my face as I cuise down the highway at 70 mph. That is why I have a windshield. If someone likes to eat bugs and feeling those rock, more power to them.
Not sure this is an age issue kinda thing. I'm 56, don't have a windshield yet, but I just about had enough rocks, sand, birds, bugs, rain and other various road debris bouncing off my grill.
Don't forget not all windshield clad bikes are created equal.Some of these machines have the ability to keep about all in their tailights.It's up to you to figure out who they are,some are easy to spot others are Sleepers.