Yes, it looks like that should be OK.

With regards to the ESD chip:

The ESD chip is going to try to prevent transient overvoltages from persisting on the protected line (which is going to be a voltage-sensitive circuit). Since (if I understand the application and schematic correctly) this circuit has a microcontroller with a data pin directly exposed to an external connector, some form of ESD protection is going to be highly recommended, as modern microcontrollers are going to be extremely intolerant of surprisingly low overvoltages.

This could happen if, as you suggest, one end of the audio cable is unplugged and a transient voltage is applied (by touching the exposed connector end), while the other end is plugged in to an instance of the board. This applies whether or not the affected board is energized (and it looks like this ESD chip will function passively, as it claims to be effectively a pile of diodes).

You do in fact need protection on both halves of the board, since they can exist as physically separate devices (e.g. when stowed for transport).

The particular ESD chip you’re using has VCC on pin 2, GND on pin 5, and four interchangeable-looking functional pins on 1 / 4 / 5 / 6. As long as you orient the VCC and GND pins correctly, you should end up with a valid circuit.

With regards to decoupling capacitors:

The main purpose of these is to filter out high-frequency noise on the voltage rails. These do serve a factor in ESD protection (which involves huge instantaneous voltages but not all that much charge), but also guard against other transient voltage variances that might affect operation or reliability of the circuit.

Because the decoupling capacitors you’re looking at are part of the ESD solution (with regards specifically to voltage rails), I wouldn’t suggest omitting them.

It’s not clear to me that I could ever listen to podcasts while playing most of my library, but I’ll do my best to list some with which I might try:

• Euro Truck Simulator 2 (and, by corollary, American Truck Simulator). If you can listen to podcasts in your car, this is basically a similar experience :)
• Super Hexagon. This is not a game about making conscious decisions, it’s too fast for that. You’d have to turn off the music, and determine whether you can retain stuff you’re listening to at the same time.
• Race The Sun. This is somewhere in the middle of the above two.
• Solace Crafting. This is a relatively bare-bones sandbox RPG with harvesting, crafting, and building elements, that doesn’t require all that much decision making, and can be played at any pace.
• Minecraft (the Java edition). You’ve probably heard of it! I recommend the Java edition due to the rich modding ecosystem; you can usually find a flavor of content that suits any purpose.
• Cities: Skylines (and, by corollary, SimCity 4). These are both world-class genre-defining city builders, which can be played at your own pace, don’t require a whole lot of active involvement, and pair well with background listening of your choice.