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You can use "connect at both ends" on a painting (in the tweak menu) to make sure both ends stay put.
And just so you know, it won't work quite as you wanted. Only physical objects can have connectors attached to them. But you can make a sculpt, group the painting with it, and make that sculpt invisible. So so that for each rope at the bottom (just a little nub is fine), and then connect the rope nubs to the plank sculpt.
Now, you can use a force applier to add "wind" to the scene that will blow those sculpts about. And because the paintings are grouped with them, they'll move the exact same way.