Mojave Safari 14 with Apple Pay no longer works when it used too

Ran into a bit of a snag.

Yesterday morning, on my 10.14 mac mini, with Safari 13 (at the time)... the Apple Pay black buttons would show up on the applepaydemo.apple.com page. My own test script would also show the button, and even apple's bag checkout would show the button.

However upon running into a loop where no matter what Apple Pay button I would click, it would make my iphone go into "Add a Card" mode (when I have added three cards already). It would never open the sheet with checkout details and saying "Use your iPhone to confirm" (like all the screenshots out there show doing with macOS Safari and Apple Pay).

So I was poking, and prodding, and one person said to sign out of iCloud on the mac and sign back in. So I did that.... thats when everything broke................

Afterwards, no more apple pay buttons on macOS safari for me. Not on my 2016 laptop, not on my 2018 mini. Neither Safari 13, or upgrading to Safari 14 would work. None of the pages that have them (test demo or otherwise) would even say apple pay is available.

Also, you know that checkbox in Safari > Preferences > Privacy, that says to enable apple pay prompts from websites? That checkbox is now entirely missing from my Safari. Its, just, not, there, anymore. It was yesterday morning with Safari 13!

I have tried connecting the phone with USB.

I have tried connecting the phone with bluetooth.

I have reboot everything.

I have reset my router.

I have signed out and in of my icloud multiple times (all using the same single Apple ID account).

When connected via USB:

The phone shows up fine in itunes.

The phone shows up in Safari's Developer menu for inspectable apps ok too.

The phone itself (its own safari), shows apple pay buttons just fine, and prompts for touch ok.

But.... nothing. All the guides and help topics I see all mention the checkboxes, and the prompt sheets, and what should happen.... but I'm having no luck, and have wasted so much time trying to get it to work again.

Resorting to forum posts now.... doubt anyone can help, because its like I'm stuck in limbo on all my macs.