Discovered while testing MC-129273.
Multiple paintings can be placed in a manner that they could not previously, as long as one painting is already present before entering the world.
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discovered while testing
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Then explain why this isn't possible in 1.14.2?

you still haven't explained

Confirmed for 1.14.4 and 19w37a, I just think that it should *always* work, not *never*. But that it works in certain cases and not others is definitely a bug.

Apparently paintings on the same surface can also completely overlap due to this. Definitely a bug.

No longer willing to be the owner of this ticket.
I am unable to reproduce this issue in 1.17.1 Pre-release 1.
it's not a bug. Painting is an entity. Same as item frame, so there can be 2 in one block