ohhh man, I have thoughts I’d like to share as I’m prepping a new practice plan for the day and going forward. It’s frustrating that I stopped playing 20 years ago after an aborted attempt at making a career. It’s interesting looking at where I am now and how many holes I had in my skills and technique because I didn’t make practice anything formal. I was cocky and now I see that I have and always have had some really sloppy habits. I’d improvise with albums and often pick apart songs by ear but not as much as I could have or should have. I too picked up on some limitations in basic pentatonic and blues scales knowledge, especuially outside of the three most used positions. The cool thing is that my ear improved greatly without touching an instrument as I have music going constantly, especially 50s and 60s jazz.
My story’s a bit similar. I started playing guitar about 40 years ago, learned some Travis picking, that kind of thing. I didn’t start taking it seriously until about 5 years ago. I’ve been having f2f fingerstyle jazz and flamenco lessons for the last 2 years, but I’ve taken that far enough - there will always be 12-year-olds in Spain who play better flamenco than I ever will - but like you I’ve started going back over old ground and apply what I’ve learned. The result is that I’m playing everything I ever played much better. I no longer rest my pinky on the guitar and that alone has improved everything. I’ve started using a pick for the first time and I’m enjoying that, too. Alex’s lessons are so ideal that they could have been written for me personally! And you’re definitely right about exposing yourself to the kind of music you want to play. Trouble is, I’m still rotating between jazz, Americana, blues and flamenco, not really focusing on one genre. I think at the moment I’m learning most from the Chord melodies (which I love playing) and the theory stuff.
One thing I’ve heard from jazz teachers several times is that anytime a student wants to learn jazz they ask the student back, “Do you listen to jazz? What do you like?” and they often can’t answer because they just think they should learn to play jazz. If you are not exposed at that basic level, it’s a silly exercise.
Blues, jazz, and Americana are pretty highly related and there is probably a hybrid style of which of those you prefer. My teacher calls it all “American Vintage Music” (flamenco is different though and very cool). There is a style that combines the American Vintage Music mentioned. These genres mix well and complement each other. Alex does a lot of country/redneck/hillbilly jazz and western swing lessons. Alex’s tastes and mine are almost identical. I’d take lessons and might one day, but a very good friend is teaching me. The problem there is that we end up kind of just hanging out instead of working.
There is nothing wrong with being genre-fluid. I like artists who mix genres. Tom Waits is good at that. I feel like Beck is the same way. There is a lot of vintage American music in even Beck’s more electronic-sounding work.
Never heard that before, love it 
“American Vintage Music” is also a great description. The funny thing about me and jazz is that I tend to listen more to artists like Miles Davis and Stan Getz than the big jazz guitar players. What I like above all is a definable melody - jazz bands that sound like a blues band falling down the stairs isn’t really my thing. Ultimately what I’d really like to do is have a solid repertoire of chord melodies in my armoury. Things like Moonlight in Vermont (I like Charlie Byrd’s version best) and Moon River (Martin Taylor). And I love gypsy jazz but I know I’ll never reach the skill level for leads. I’d be quite happy to try the rhythm parts though. Alex’s Bossa Dorado is on my list, which is getting longer and longer…
I am kind of the same way with jazz guitar players as well, or was until I heard grant green. I had Kenny Burrel Midnight Blue because that’s the law. Later I foiund the swing guitar players who generally tried to sound like horn players, Charlie Christian, Tiny Grimes, Bill Jennings stuff. A lot of those post wat jazzers were trying to cop later young anyway. In general I’m into more hard bop and particularly almost anything on Blue Note until the early 60s. Hank Mobley is MY MAN.
I love almost anything related to Art Blakey’s Jazz Messengers, Horace Silver, Clifford Brown is my favorite trumpet player.
Some new names for me there so I’ll be checking them out, thanks. I’ll be giving Kenny Burrel’s Midnight Blue a spin as soon as I finish typing this, having it on vinyl is the law too 
I think Alex has done a Kenny Burrel lesson, I’ll have a look. Btw, I see he’s still with us, aged 92 now! Kenny, I mean, not Alex.
Here he is, playing as a young whippersnapper in his mid-eighties.
Amazing work mate, you have the rhythm feel totally down… love it! 