@Mr.Si:
However, I feel as though if an update is made available as a release and is reported as successfully updated, then the thing should work. Or is that too much to ask?
Did you read the individual release notes of the updates? Did you remove all aditional packages before updating, as advised? Why where you that much behind with your pfSense version? Did you do any custom modifications off the OS and did you undo them before trying to update?