All other things being equal, the second woofer will lower distortion in the frequency range where every speaker has the highest distortion–the bass.
Now, if you like the 20s and find their low end balanced and still to your liking when the volume goes up, it’s probably not worth it.
EDM to modern dance for whatever reason, can sound fucking mega. Daft Punk on vinyl is the only way to fly. Same with Major Lazer & LCD Soundsystem.
Your reasoning for thick speaker cables may apply for pro-sound, but the “home audio reason” is that DC resistance is the enemy to a speaker. It fucks with the bass response, effectively raising Qes and throwing off the whole enclosure alignment. Like the effects of power compression, but all the time.
And the lower the impedance of the bass driver, the worse this impact becomes. An 8 ohm speaker could probably be run 50’ on 16ga without obvious audible issues. A 4 ohm…you just might.
It costs nothing to try. That’s the key bit.
There’s no single answer, but almost every speaker will benefit from the reduced side wall interactions since the walls become even more off-axis with regard to the tweeters. And heck, constant directivity speakers often sound better with even more toe, to the point where they’re crossed some 16" or more in front of the listener.
Toe in is as much about the interaction between the speaker and the room as it is between you and the speaker.