TouchBar will play nice with digital audio workstations like Logic Pro / Live, etc. I'll be happy to record pitch/mod/any VST param automations on a touch strip.
DJ-ing apps could show up cue points and let you trigger them.
While fullscreen mode on macOS advocated distraction-free focus, TouchBar takes a step backwards.
Monokai is popular choice for many initially, it looks good but hurts eyes. Solarized on the other hand seems to lack contrasts at times.
After spending a great amount of time in 'Merbivore Soft', then 'Made of Code' last year, I've fallen in love with 'Tomorrow' - ST2 & XCode. Mostly for the vibrant colors and pleasant contrast. Clojure too looks very nice in this.
Good luck! Doing contract work as a web/app developer brings in good money (depending on what your expenses are), and also leaves free time (depending on what you charge hourly).
I'm trying the same since July. One of the important lessons I learnt on the way - be super-serious about organising your time. July & half of August flew away in a jiffy as I was trying to do/learn too many (mostly new) things at the same time. I'm trying to form habits around the way I spend time, not letting new ideas distract me on a daily basis.
You've been working in a jungle of roles for 8 years, bet that bit wont be hard. Good luck again :)