Nextcloud is feature-rich, but a little slower and vastly more complicated than a CalDAV server like Baikal.

Uh, can’t you just log in to online banking through a browser? I can.

Grep. If you have the sources digitally and local, you can just run a search for a string.

Don’t use Outlook for non-Outlook email services. Problem solved. I am required to use Outlook for my work email, but I keep all of my personal email separate, accessed with FOSS email clients.

If Hugo stops working down the line, you can compile your markdown with something else. Simple is king!

Not my experience at all. Once my OpenSMTPD mail server was set up 3 years ago, the only time I spend on it is updates (like 20 minutes per year). Setup did take some time, but it was totally worth it to me.