XD Jacob has good reason to be paranoid here, at least. They are but small grains of rice to him. He’ll have to watch out when he talks. Little guys like that can’t take a lot of volume from someone his size! Plus on the other hand, Jacob might not hear them if they say something to him (Bowman would be pissed if he couldn’t scold Jacob).
Regular Sam at least has a bit of experience climbing sharp cliffs, like elevator shafts, though the smol versions of him take it to a whole new level! He’d be fascinated to see one of him climb himself, especially since he knows he’s a tall guy.
The folds would be pretty intricately detailed. A normal smol could easily fit their fingers through the holes of most fabrics (especially the flannel that the Winchesters wear), so someone that’s that much smaller might be able to stick their entire arm in. @.@ That’s a lot of fabric.