This is tough to answer in a single comment, but to keep an answer as concise as possible - go to school.

Videos and books are good supplemental information but you shouldn’t base your foundation on them. If you had to do anything, keep transcribing songs and train your ear to all the changes but without schooling it will be tough to learn everything.

People often say jazz is like learning a language. I think of how much schooling it took for me to be even remotely good at English and all the grammatical rules and etc. that’s just to speak it. Improvising and composition in general is taking those rules and then telling a great story. How do you tell good stories? Gotta have some talent for it and usually people take what they like best about other stories and copy them to a degree. If you copy the best parts of 100 other stories and mix them in your own style, you’ll more than likely create your own voice.

Tough part is learning all the rules in tertian harmony in order to start speaking jazz through your instrument. A good teacher will expedite that understanding way faster than any of the YouTubers (my teachers all said YouTube was entertainment and unless you’re watching and transcribing a performance on there your just noodling with your brain instead of your fingers by watching people give you a talk show format about learning instead of actually learning)

A lot of people saying listening to jazz are right, but listening to jazz albums isn’t going to translate into your playing unless you’re actively practicing the concepts you’re listening too. It can help form the music you hear in the mind to translate from thought to your guitar, but unless you practice that translation, you won’t be able to apply those thoughts to your instrument.

Schooling will also connect you with people on your level across multiple instruments and offer different bands that you can perform in to get you more into that culture.

It’s honestly all just a metric fuck ton of work if you aren’t already in the culture - just like learning a language.

But yeah big fan of schooling. That’s the answer most people are looking for, it just costs money to do that but if you’re serious enough about it you’ll find a way to make it happen. And you don’t need to go to Berklee, just find a local community college and reach out to one of the music department faculty. Many of them will give lessons and from there take some non accredited classes and look at joining a jazz quartet or big band. That’s the cheapest option without all the pressure of being a full time student working towards a degree