With endings, I can't explain it but I have very strong feelings about proportion and when it is OK to end. Maybe it's a need for evenness, maybe it's a need for balance, maybe it's something else. But looking back, I still feel that that tune ended exactly when it should have. I know that John felt differently, but he's too much of a gentleman to make a scene when I kept playing, so...
This brings up another interesting point - namely that of harmonic rhythm. I find many jazz reharms distasteful because they often seem to insert chords because they can without consideration for how janky the harmonic rhythm feels when the flow goes from
chord chord chord chord to
chordchordchordchordchord and back again. It doesn't have to remain constant, but it is a part of the flow, and I feel this is worthy of consideration, even if only on the intuitive level of knowing when it
feels right. One of my personal pet annoyances in jazz is chains of sideslipping ii-V's inserted into a progression that I don't feel needs them. The third 8 bar phrase of "Blackbird" strikes me this way; it doesn't need all of those ii chords, and it takes a pretty great melodic player to cover those changes without simply sequencing the same idea down in half steps. I much prefer the simpler path on this and most tunes. The rick of playing the V of the ii-V's is a more natural sound to my ear, which is why I tend to do it more often than not.
But cobbling together your own harmonization of any tune is a great practice to get into. By doing this, you're getting deeper into the tune and coming up with something that feels right to you, which is always good.
I think this is pretty much on point. By simplifying you are not only making existing pathways clearer and easier to implement, but you are also opening the door for variation/deviation from a predetermined set of actions that is on autopilot; programming your own safety net or safety zone, so to speak, so that you can afford to take chances spinning variations on it.
Kind of like the above, when you have ingrained the simplest path through the changes that still supports the roof, the many variations flow from that. In the first line of the tune, the simplest changes just sound "F Major". In the practice room, you might practice many different tricks for elaborating static tonalities that last 4 bars in a melodic sense. The second set of changes that go I - IV - iii - V7/ii- ii - V7 - I are a perfect example of a "round trip turnaround", or what I think of as "treading water" harmonically. You are free to play more imaginary changes than are actually there at any given time if you feel it gives your line more forward motion, just as you are free to mentally simplify changes by eliminating the decorative changes and play the big picture. The beauty of it is that each line is its own layer of counterpoint, and that different layers of conception can be happening at the same time. If the changes are organic, the busy harmony is just one possible outcome of the static harmony; so if one player decides to go totally static and play a dominant pedal over a tonic harmony while the other player decides to outline the busiest set of changes he or she can think of, it all still works as long as the resolution happens together.
The following short example of the first line 8 bars of the song illustrates this (I hope):