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> Gmail is free

Perhaps this is a bit doctrinaire, but it's an important distinction:

You pay for Gmail with your privacy and personal information (you can say they are worthless to you, but you do pay). OpenBSD is truly free-as-in-beer.

You also have no end-user control or 'freedom to tinker' with Gmail. OpenBSD is free-as-in-speech, also.

You have to ACT proactively to upgrade OpenBSD, unlike gmail.

> Gmail is free, would you be happy if they updated it and your email didn't work anymore?

I would shrug, meh and do something else.

I've had my lifestyle made illegal a couple of times. Perspective.

The last and only major PF syntax change was, what, 5 years ago now ? 4 years ago ? Any other changes are relatively minor and reflect other changes, such as features being removed or added.