Thank you for your long and detailed reply. I am glad you like it and appreciate some of the more targeted feedback.
A chain gang was indeed on my mind when I wrote it. 'Oh Brother where Art Thou's imagery has been burnt into my mind at this point and I maybe dug even more into that well that straight up western just as you suggested.
I try to find ways to emulate the production techniques of what I am referencing, so I tried to have a modern take on the boom bap tracks. I sampled old rare groove songs, splitting the individual voices with an app and then treating them with low pass and other effects. I cut them up and treated them in many ways so the original sound is no longer present. The warbly record scratch effect is an old group jazz impro, that I cut up and treated with a tape delay, automating the delay time that I had set to a note value. This led to them jumping between the reverb values in a jerky manner almost like manipulating a vinyl record. Just as the rap producers, you sometimes have to use gear in a way that isn't intended.
I am certain that the Pirate track hits the master bus a little hard at times. The loud low strings are intentional, but I might have toned it down if I had some more time - the finer nuances can get lost in such a tight timeframe, but I also was kind of numb to the track as it ate a lot of my time for the jam, while others were written in a more spontaneous manner.
Also thank you for noticing the sound design in the first couple tracks, particularly the short interlude. That one was done similarly quickly, but I just enjoy delay effects so much, it was a joy to experiment.