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Disclaimer: I've only been dipping my toe into the "OpenBSD as a daily driver" water since 7.1

Updates can be terrifying.  When I was younger, going from Windows 3.x to 95 meant various games would break.  At work, updating the varioux Linux distros and patching Windows
is absolutely terrifying in some of the environments. Obviously some past update-trauma to work through.  Optional and needlessly long background: [*BSD as an operating system was always spoken about with the same combination
of fear and reverance as Solaris and Unix, both at school and at work.  It was sort of like images of deep space: We all enjoyed looking at them briefly but have zero appreciation for
the technical feats that got them to us.  That started to change and soften a bit when OS X came out and everyone reveled in how wonderful an implementation of BSD/Darwin/Mach it was.
A few classes on Linux and Solaris along with a couple job's worth of trial by fire in AIX and Solaris in a production environment made the thought of one of the BSD OS's as a daily driver
less daunting.  When I finally turned in my work MacBook, I tracked down a decent ThinkPad and dove in.]

pkg_add -u

It's borderline magic.  I've run it on laptops, servers and my lone, tiny Thinkstation desktop I pieced together from Desktop team's recycle bin.  It's run without causing a fire or too much heartburn (some of the sysmerge questions are scary at first, but once you read through them a couple times they will make sense - especially if you have some custom configs or SSH settings that might not be standard).  Some scenarios I'd like to test next:

virtualized OpenBSD
32-bit OpenBSD
Manual upgrade (e.g. the more than one rev behind - is it essentially just 2 sysupgrades to get it current?  Or is a manual upgrade the only method?)

Further reading:
https://www.openbsd.org/faq/upgrade74.html (OpenBSD 7.3 -> 7.4 Upgrade Guide)
https://dataswamp.org/~solene/2023-10-01-octopenbsd-2023-openbsd-intro.html (Solene's Intro to OpenBSD post)