1) internal company webapps just install company root cert and create properly signed certs under corporate internal CA. Installing the certificate across network is easily automatable on windows, OSX and Linux. The only issue is Firefox as it uses its own trust store. Any senior admin who can't figure it out with the resources available (plenty of information available online) should be replaced days it is not that hard.

2) with regards to raspberry pi, will anyone who can write code can learn to also create their own CA the only difference is probably no automation of adding to the trust store likely however it is only a 2-3 click install in most cases.