I think you reading to much into my comment. I did not meant that specifically FreeBsd needs an extra attention.
What I meant is that dockerizing your applications (which author of article seems to have a problem with) is easier from that point of view. There is no need to provide a package for each distribution or OS you want to support. You can bundle all the necessary dependencies if there are any (like i.e. databases which author provide as an example of unnecessary redundancy). There are solutions for web managing docker containers and stacks like Portainer, Taisun, Yacht and probably more I am not aware of. You have Watchtower and Diun for update notifications. So it is simpler for developers and partially for an user.
Maybe there are similar solutions for FreeBsd package manager, but this is only for FreeBsd. With docker it should work on every environment that can run docker. So again it is simpler.
You can run your services without docker and sometimes it is easier without it (i.e. running DLNA server) still, I would not want to run my email server as nginx/postfix/dovecot/sogo/mysql as separate services that I need to separately install, configure and update. There are dockerized solutions for that that exists already that you can start and run with docker + some DNS config. It is just easier.
If you are fine with your stack on FreeBsd it is totally fine, but there is a reason why less, or non-technical people are running commercial NAS devices like Synology. Because it is easier.
And there is a reason why non-technical people are using Google Drive and iCloud for their needs like files sync, backups and email instead of running their own mail server and NAS: because it is easier.
So I do not have anything against FreeBsd and their native packages. But you wrote yourself:
> about once a week I run a pkg update, pkg upgrade and service x reload in each jail to update the software and 99.9% of the time it works smoothly. It really doesn't get much simpler than that.
Yes it does: web or phone app management. Why you have an app for every silly smart devices people are buying (like i.e. smart fridge or smart dishwasher)? Because it is easier for ordinary people. Samsung and LG do not make CLI for those to manage those devices via SSH. Maybe it would be even easier, once you are familiar with that, but people are not. Try to explain your hairdresser or plumber what is FreeBsd, pkg, jails and services.
> This could also be done with cron like in your example, but I don't think automating updates is such a great idea. I think updates should be monitored.
Which is exactly why I wrote that I, personally, do not want to spend few hours every week to upgrade and monitor upgrade process of all my devices. Especially since those are used by my family and I do not want to update them during a day, because they will be complaining that they can't use something. And I do not want to do that at night because I want to sleep. I you have nice solution for running 10 or 20 applications on FreeBsd, with very easy and quick update and backup process for them, please write about it. My solution takes about 2 hours every day for 4 devices and about 6 hours of update and backup - every day. But sending about of 2TB of data backups (even incremental) must take some time.
So, again, I agree with an author with few points but in an essence, I do not agree. I does not matter if you use FreeBsd, or Ubuntu or Debian or UnRaid for your self hosting needs. We need simpler solutions for self hosting for ordinary people.