'Upgrades are so safe they're almost boring'
You have *got* to be kidding me. So far I've found FreeBSD upgrades to be somewhat of a pain, and FreeBSD has ongoing issues where you install a new package, it breaks something else, and then you have to do an update of everything, cross your fingers, and hope. At that point you wonder why you're not using Windows instead. Upgrades are also quite slow, even on reasonably recent hardware.
I persevere because I'd like FreeBSD to succeed, but given the increasing polarisation of operating systems you're still hit over the head repeatedly with the fact this is Not Linux or Not Windows. Last weekend it was even worse, a project to install new firmware on smart plugs is not only Linux specific, it's *Ubuntu* specific ('needs Network Manager and Docker, not tested on anything else'). Mint appeared to be close enough. Ubuntu didn't boot or possibly was grindingly slow (Mint was glacial to install) on the old Athlon system I tried, apparently the Windowsisation of Linux continues. Not using a particularly modern system? Prepare to experience pain.
On the other hand for the most part OpenBSD really is fire and forget. Run sysupgrade. Go to make a cup of tea. Come back. Done. Provided you're sticking to functionality in base it's pretty straightforward. (OK, technically I did run into an issue a few releases back with an old system with only IDE support and an unusual partition layout, but that's a rarely used system).
No surprise about Wi-fi. I gave up on that under OpenBSD and others, it's one area where it really needs the manufacturer writing the drivers. Stopped trying to create my own access point or failover to a 4G dongle, an moved to a standalone access point and 4G router (running Microtik's RouterOS in the latter case)