Yep, that's sexism in action, alright. He's exactly part of the problem, and the fact that he's resistant to changing it just shows how pervasive it is.
Yes. Especially if you include platform faux-pas in "aesthetics". One of the worst offenders is when someone makes something "cross platform" while ignoring all the conventions of all platforms except their primary dev platform. Generally speaking, those lead to an immediate uninstall, since they're so awful to do anything with.
Access is well known as being the anti-database that no one should ever use, but people still think Publisher is still acceptable for producing documents for print. DIE PUBLISHER DIE.
I've got a relatively new Vertex 2 which is totally fine, but that's still well within the realm of normalcy. However, I've also got a first gen x25-m, and that is fairly old as far as SSDs go. That one also still works perfectly.