Hope you like that book. I used to teach a class w/it eons ago. It always inspired a lot of heated discussion. I mean HEATED!
About the particular edition of the chorales you mention - it's laid out fabulously. But the chords as they're labeled are often very wrong. It doesn't mean it's a bad book ... it's just that it's not an authoritative book that's been edited, reviewed, etc. by peers and colleagues. And as an analysis of the chorales it's a place to start ...
Unfortunately there isn't yet a book that shows directly how to use the gold mine of the chorales in jazz. The closest thing I know of is a Downbeat masterclass article w/Fred Hersch where he describes his approach to it. If you have questions about it just let me know ...
If you have a classical ed. - and you've already mentioned good books you- read in that vein - then you've got something on which to build. Jazz definitely has a lot of stuff in common with classical music. Look at transcriptions (or even do some transcribing) and it's there to be seen.
These days the best 2 counterpoint books are probably by Peter Schubert. He teaches counterpoint from written and improvised points of view. I still think Schoenberg's Theory of Harmony is the best book on chorale style harmony. But everyone has their favourite harmony book - for classical and/or jazz
About Monk and his style ... there's all kinds of stories about him. But there's also an excellent detailed biography - Thelonious Monk, the LIfe and Times of an American Original - with a lot of stuff in it that was previously maybe not totally known. Basically, Monk had very serious, comprehensive classical training. He could play anything and he knew a lot. No surprises there
Through the 40s and into the early 50s he had a hard time getting steady gigs. So he was known in those days as a teacher to a lot of young jazz musicians. If anything he was seriously generous with his knowledge in those days. At least according to the book I mentioned. He also always had serious emphasis on finding his own style. Which in general was the ethos of the day.
I can hear in your Soundcloud recording ... the boogie one that the vocal stuff has some great voice leading going on. Very nice arrangement.
There's an amazingly talented guy in London - he's probably not yet 20 - who has some great stuff on Youtube.https://m.youtube.com/watch?v=K28H04Y2IdE