The transparency is refreshing. The details for Server2 show some hardware info as well as the max number of VMs. I've never seen that before and wish other organizations would follow suit.
I also like that they publicly state their support for the OpenBSD Foundation. Given the transparency about their approximate userbase and donation amounts, one could even roughly predict how much they will donate per year. Among other things on the site this makes me trust them more, as it's not the info you'd expect from an untrustworthy person.
For as long as the release is supported you can use syspatch(8). They also appear to provide serial console access on request so you can perform a release upgrade via the recommended bsd.rd (RAMDISK) kernel method.
You can do unattended upgrades using autoinstall(8). There is a handy script for patching bsd.rd with a configuration file for the update process: https://bitbucket.org/semarie/upobsd/src although there should not be anything to configure on most boxes (maybe you want to deselect the X packages for your router).
I also like that they publicly state their support for the OpenBSD Foundation. Given the transparency about their approximate userbase and donation amounts, one could even roughly predict how much they will donate per year. Among other things on the site this makes me trust them more, as it's not the info you'd expect from an untrustworthy person.
Good luck!