You can install your own CA certificate in the user certificate store, and it will be trusted by Chrome and any other app which opts into user-installed CAs, which should include email and calendar apps.
What is unlikely to work is installing your own CA and using it to intercept traffic between apps and the app-makers' servers. That sucks - you should be able to inspect what your own device is doing - but your use case of using a private PKI for your self-hosted software is definitely supported.
It doesn't matter how often it happens. It's a vulnerability that people will end up being exploited or the data will end up being stolen by another hacker.
Not all banks allow desktop usage. Some banks restrict certain functionality from the web interface since it is less secure.
It absolutely matters how often it happens. Otherwise we should start imprisoning everyone in the hopes of getting that one serial killer by the same principle. Some cures are worse than the disease.
What is unlikely to work is installing your own CA and using it to intercept traffic between apps and the app-makers' servers. That sucks - you should be able to inspect what your own device is doing - but your use case of using a private PKI for your self-hosted software is definitely supported.