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.

OpenBSD

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

I just finished upgrading my three machines with no problems; some issues with updating packages. May be wise to wait so that repositories are synced..

OpenSMTPD. I run a private mail server for family, and it works flawlessly. No maintenance aside from backups and occasional OS upgrades. https://poolp.org/posts/2019-09-14/setting-up-a-mail-server-with-opensmtpd-dovecot-and-rspamd/

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.

Doesn't work with Javascript blocked.

personal

Decent used laptops are quite affordable. I recently scored one on Ebay for under $100. It runs Linux and everything is snappy.

No.

Laptop not a server, huh? I am writing this from a laptop running OpenBSD, which is my main work and play machine. Works great.

Makes sense for interoperability with other scripts. Thank you.

My OpenBSD operating system on my laptop is set to randomize my MAC address at every boot.

It involves a learning curve, and some things don't work like bluetooth and streaming copyrighted movies. But most everything else works. Many things in AUR would not be there, but alteratives exist for those willing to adapt. Setting things up are typically done by editing text files on the command line. This sounds hard, but is actually simple once you get used to it. I tried Qubes last year out of curiosity and found it hopelessly convoluted.

Use a hardened-by-default OS like OpenBSD, HardenedBSD, or something similar in Linux.

Thanks for the explanation.

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

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

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