Well, not having lived your life, it is hard to say... you might be the smartest person in the room but have trouble communicating with others in a way that makes them trust your take on things. Or you might not be the smartest person in the room and are not hearing the reasons why everyone else is doing things you disagree with. Either way, it sounds like there are communications problems acting as barriers within your teams. This is really common, so that isn't a diss in any way. But not having lived the same experiences you did, I can't say specifically what the problems are... all I can say is that the level of frustration you are sharing is often rooted in a lack of understanding between team members.
Except I'm pretty sure that I'm a good communicator. Background in sales and performing arts, mentoring and presenting are some of my strengths. I'm always immensely popular among my peers and I'm usually quite chill when it comes to horse trading and picking which hills to die on (isn't HTTPS one of those hills?). I appreciate that its probably a chip on my shoulder that's preventing self growth but I can't but feel a combination of youthful looks and lack of degree is the reason I seem to be constantly forced to prove myself again and again and again, despite often being one of the stronger technical members in the circle.
Maybe I've just got to do a better job of seeding ideas, so people think the ideas are theirs and accept them better. Maybe give them the ingredients of a very obvious sandwich instead of making it for them. Idk, I just can't help but feel discriminated against somehow because it doesn't make any sense to me to; not installing a cert on a server and rather forcing people to send their creds over clear; being vehemently opposed to using Sqlite (in more than one org!) when its an extremely appropriate option (in embedded or as an MSAccess replacement). Maybe on that http issue I should have followed my first thought and collected and sent that guy his own password to demonstrate the issue.