I'm on Team Play it Your Way. You have been wanting to go shorter for a while, which is a pretty good indication of where your heart is at. And we know it suits you!
In my 20s I cut my hair really short like this. An older, more sophisticated (and European) friend said to me, "I am so glad you really cut your hair and went for a super short cut. There is nothing less stylish than one of those short cuts that is neither here nor there."
That remark has always stayed with me to the point where I worry if my short hair seems to be getting too "long." Ha!
I just got a cut and my stylist made it really short back and sides but left length on the bangs. Like you, I need them thinned a lot and also need to flat iron them in humidity. Or sleep on them. If they bug me too much I am going to get a more textured shorter cut.