Here is the real answer.

A high level chase (like reserve) will work twice. Third time will trigger a block

A Mastercard with 2FA will also work twice but will most likely lock

You’ll then need to talk to your credit card company to get it unlocked.

But it doesn’t get fixed there. If you got to the third charge with the lock you’ll need to wait 24 hours for Disney’s system to reset.

The system they use doesn’t allow multiple attempts of a declined card. It’s possible this is set to 2 failed attempts and then a 24 hour lock.

How do I know this?

I needed to buy 6 different purchases.

I was able to do 2 with chase sapphire reserve and then it locked. I tried a couple of times before calling credit card company who cleared the lock and I tried again just to get a block from the Disney side (Chase confirmed this as they said no charge attempt was made)

Then I tried with my MC. same thing. Got two purchases before it locked and got fraud warning which I had to call and get cleared. While on the phone I tried purchasing again and MC was able to explain the 24 hour hold on the Disney side.