@Cabledude
My 5 cents :
Is it always good to update pfSense?
Yes, it is.
That is : do not update / upgrade the moment it comes out.
Take your phone, set a rdv at 'now' + 2 weeks.
During these two weeks, look at all the forum message that talk about this new version.
If issues are mentioned, like "FreeRadius plays hardball with the new PEAP protocol when using vlan and radius capable access points" then you know : that issue won't concern you.
If it says : "the DHCP client on WAN doesn't work anymore" then you now there's a show stopper out there, and you change de rdv set to "2 weeks" and make that "1 month" and you go back to normal live for the rest of the month.
When you use the same version as everybody else, you have one huge advantage : if you find an issue, you can't be the first one that found this issue. So ... your issue is already handled and answered on the forum.
Issues can't survive if hundreds of thousands of user have the same issue : they get dealt with.
If you use pfSense Plus, you have ZFS, live gets even easier on you : create a new boot environment, boot into it, and then upgrade. Something doesn't please you and you have no time dealing with it on the spot : boot back into the previous environment and call it a day, deal with it later. "Let the forum tell you later what to do".
The ZFS file system allows me to use the Beta versions, which is normally a big no-no if pfSense is used in a production environment** as I know I can get back to a working condition the time it takes to reboot, 60 seconds or so ?!
I would the contrary is valid : if you have enough expertise, enough time to lose, you feel right at home at the command line, editing a script file here, patch something else there, you know the basics of the OS used (FreeBSD), you control the sate of your router regulatory, always on the look out the event in the system logs that is 'new' or 'strange', then, yeah, you might be qualified for the "I don't upgrade' option.
Guess what ? Experts and the ones who know what they are doing, don't do this 😊
** or a simple 'home' setup and you have 15 years old as network clients, then using the Beta version can condemn you to sleep in the dog house.