I see a couple different topics here. Real life never lives up to the fantacy. Sure, lots of things would be easier if we were born in our preferred gender. That's a given.
As for the Maculinity and Femininity debate... tale as old as time. I don't believe that masculinity is valued more. In fact, Masculinity and Feminity aren't really the issue. It's when they lump "self confidence" and "self sufficiency" into being Masculine, and the "neediness" of the damsel in distress into femininity that you have the issues. Nobody wants to deal with constantly helpless/needy people, especially in the work place. The softer spoken feminine response can be every bit as direct as the masculine one when supervising or reporting. It's still all in your self confidence. Where as the unsure "damsel in distress" response would come off wishy washy. Using the Damsel in destress approach to contanstly need assistance with a task will also get old. Self reliance is again the key, rather than Masculine/Feminine. You can take many scenarios and it still comes back to that.
I personally go for a highly feminine appearance and attitude/persona, but I also try to exude self confidence and self reliance. I have never really been faulted for anything relating to my dress, or nails; or hair for that matter. I do get called out for looking nicer than the occasion has called for, but that's nothing more than pride in one's appearance. I still run a grinder in the shop like a champ, no question. I still have no problem telling someone that they screwed up or did a great, in no uncertain terms. Feminine responses are typically more articulate than the Masculine responses, but both get the point across. However the feminine response is less likely to create animosity, a far better quality to have in my opinion.