Oh, yes, here's another post to note that there were additional syntax and structural changes to PF at 5.5 for queuing. There was a transition period for two releases... one year ... to assist with that transition.
Throughout the intervening years, there have been many built-in application changes. Without thinking much about it, I recall major changes in Mail Transfer Agents (sendmail is long gone), web servers (OpenBSD's fork of Apache 1.3 -> nginx -> httpd). Huge changes in daemon management.
A transition of existing applications and services to a new, clean system will be much easier on you, and on those who use your servers.
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