We have 2 sites. I, dev, set the https system for one in 10 minutes. The sys admin has been working on it for two hours already and he doesn't want help

That is called Ego

Maybe it's not your case but our dev also complains when nothing works in staging environment ..when debugging the dev environment we figured out they chmod 777 everywhere they launch all services with root ,they were not giving a single f*ck about securing web servers