Why would dipping a cold item in chocolate "help" with tempering?
To answer your last question: yes.

Regarding the previous question, it's because the temperature at which the cocoa butter in the chocolate crystallizes affects the overall consistency of the chocolate. If you've ever eaten a chocolate bar that was left in a car on a hot day after it has cooled down again, and who hasn't, you'll know about this. Sometimes chocolate tastes fine but has a definite 'grittiness' to it: other things being equal, that's usually because the cocoa butter crystals are too large.

Cocoa butter has a number of different crystal forms, each of which will have a slightly different effect on texture and melting point. When melted chocolate sets, the cocoa butter crystallizes, and it will generally all crystallize with the structure that it starts to crystallize with. (This process where crystals start to grow is called nucleation.)

So you want to have control over the temperature at which crystallization starts. The optimum crystal form for nice chocolate will tend to predominate when crystallization starts somewhere between 18-25 degrees C (around 64-77F).

So if you think about it: when you add room temperature stuff (like a pretzel) to chocolate that is considerably hotter than room temperature, the resultant temperature on the surface of that pretzel will likely be way higher than 18-25 degrees. On the other hand, if you are dipping an item that is significantly below room temp, then your chances of hitting that window are much higher.

The surface structure of the thing being dipped can of course make a difference to crystallization as well, but for normal purposes that is marginal. To put it another way, it doesn't matter what ingredients you're dipping - temperature is key!