To add meat to these bones, I've played piano on average 20 minutes a day for 22 years. That means ~2700 hours of piano practice. Probably an underestimate but it does match my intuition of thousands of hours.
I’ve lately been playing through the “real book”, sketching out each song quickly and doing a run through, maybe 8 songs per day.
In just three months I’m on my third time through and have discovered probably 100 songs I just love to play that I’d never heard before (Ellington is a genius songwriter. “Cottontail” is one that I get excited to see when I flip to it, and I just have to play at least three times).
Not actually a big jazz fan. I like simple consonant sounds and cute melodies, so I skip the bop, Mingus etc. My absolute favorite is when the whole song is cute and tidy except for one accentuated bit of dissonance that comes smashing in when you’re not expecting it, then waltzes right back out, transitioning perfectly into the next section and leaving you shaking your head in awe. The Beatles were masters at this.
My sight chording/inverting and rhythm reading has gone through the roof. It’s like an endless jigsaw puzzle.
On a song like cottontail, I still can’t play it perfectly at speed, so I’ll stick to what’s written until I can.
I fudge together a metronomic base line in the left hand and voice all chords with the right hand so the melody note is at the top (I don’t play the root in the right hand unless it’s the melody note).
Once I can do that easily without any halting or mistakes, I’ll start to improvise.
Wouldn’t dare to play with “real” players as I often haven’t heard the recording and am blissfully unaware of the missing comping, licks, etc. Most of the time when I finally listen to the recording of a song I love, I don’t even like it. No one plays the melody and everyone’s showing off. It’s fun to experience live, but often sounds too busy and aggressive as a recording.
I guess that’s a matter of taste. I enjoy sparse music unless it’s rigorously orchestrated (eg I love listening to Cuban music, which is quite busy, but everything fits together perfectly)