Alright. Well, this isn't too far from what I've been doing all these years.
It sounds from your op, that you're already on-track as far as playing music with others. That's good! There is no better education than playing with others- particularly playing with other musicians that are BETTER than you! The hired-gun thing requires experience playing different styles & feels and being able to gel with players coming from different perspectives. That means being able to hang with solid drummers, crappy drummers, esoteric soloists, deaf guitarists, etc, etc....
People skills are so important. Be sure that you're the kind of person that people really want to be around. Being nice & having a sense of humor are absolutely necessary. I've developed a mantra: The first 2 gigs are 80% playing skills and 20% people skills - every gig after that is 20% playing skills and 80% people skills! No joke.
Location, location, location! If you want work with established acts, you need to go where they are! (until you hit a certain level anyways) That might mean NY, L.A., Nashville, Atlanta, New Orleans, etc... Depends on your focus & where the hot scenes are when you're ready.
Music school might be a good idea for you, but honestly from what I've seen, the more reputable schools are a smarter bet. Again, the contacts and networking are key! You'll learn more about playing from private instruction & playing with others than you will from classes.
Don't paint yourself into a corner. Develop another marketable skill/ career path!
That's all the advice I can think of. Stay healthy & remember that at the end of the day, for-hire musicians are no different than any other service provider (like a plumber, electrician, whatever): your job is to make other people happy. That isn't easy & it's definitle NOT all about the music!
You should post over in the Justin Meldal Johnson forum. He's a first-call sideman with an amazing resume (makes me look like a chump!), has been to music school (I believe) & is probably the best guy to ask about this stuff!
Free advice from real pros online. Wish I had talkbass 20 years ago!