“ok, now add a metric shit ton of swearing and further belittle parsers who can’t deal with tabs.”

I would start by checking for any sort of errors in your system logs, such as /var/log/syslog or using dmesg -w. In my experience, Linux is almost universally faster than Windows.

Maybe I don’t understand the problem but the only time that pinentry pops up for me is when I am signing something. What sort of situations does it just randomly pop up or what sort of specific apps/configuration would that happen at random?

To me, zfs is like the Gentoo of file systems. If you actually use the zfs features and do a lot of digging and experimentation before you go all in on it, it’s not bad; it really can be quite good. If someone wants a filesystem that they format and forget, ext4 and xfs are still solid options. I used to use ext4 for most of my filesystem needs and xfs for my long term storage on top of mdadm. I just really wanted zfs snapshots.

Well I didn’t have that on my bingo card.

This is a similar reason as to why I use Debian as my base operating system and for just about every service I run on my host, the processes are containerized using Docker. It gives me the flexibility to choose the best “operating system” that supports the software I want to run at the release cadence that suits how I want to consume it for a given piece of software, and the base host OS is just that and nothing more. Upgrades to new Debian releases are non-events and I get no surprises with my apps in containers.

I can upgrade the underlying container base operating systems as I need which I choose Alpine, Debian, and Ubuntu based on which fits my needs. Alpine gets updates quickly, Debian is good for core services that I would normally run natively on my host, and Ubuntu hits well for wide support of almost every other service I need. So I get a stable base with the option to go as quickly as I need if I have a need for a newer package. It’s not always about having the newest software, it’s about stability where it counts.