I was very wary about the jump to 14 due to the change in Openssl from 1.1 to 3.0 and the pain that might entail. Also the deprecation of portsnap and getting used to Git was just something I did not have time for.
As I have created a new mirror site , see earlier post, I finally decided to bite the bullet over the festive break and did the freebsd-update upgrade option to 14.2, skipping out 14.0 and 14.1 in the process.
I was a little daunted and it failed to automatically upgrade everything to openssl 3.0 and although built the kernel and rebooted nicely, user land was still doggedly sticking to 1.1. I tried tinkering with make.conf in /etc with various default entries for openssl , but in the end removing the ssl version and just ssl=openssl and then making the usr/ports/openssl allowed 3.0 to install side by side with 1.1 thereby not breaking SSH or anything else until I was able to rebuild all of user land port by port. I was then able to complete freebsd-update install and now have another stable freebsd server for testing and training purposes.
Now I only need to fire this box up when I need Samba to move files around the network or download stuff off YouTube or run a Clamav as a 2nd pass for AV scanning and when I have time to dabble some more with FreeBSD.