Also annoying is never knowing how deep the menu tree is. I have to write down (or hold my fingers out) what the best option/number at the time, because its likely to change as the resolution of options refines.
Lots of internal web services, web servers, VM hosts, MQ channels, LDAP stores, etc (times 5, for different platforms and locations). Everything gets a cert, haven't been using wildcards. Lots of internal signed certs, but they suffer the same problems that this service is trying to solve.