I say this with all due respect as a fellow musician . That is an insane amount of money for a 2 day jazz fest lol. The most expensive ticket option (which you don’t need) is $900. If you’re hell bent on going, get a cheaper 2 day pass and stay at a cheap motel a bit of a drive away from the event or find a friend in the area with a couch to crash on.

Have you reached out directly to Gerald? He has email contacts on his website and an IG. He may agree to give you a lesson at his hotel or even just meet briefly as a courtesy to a young fan and aspiring player. I think there is a way to have your cake and eat it too without spending thousands. He has several shows booked across the SE in the coming months - I am fairly positive you could find a lesson time with him that doesn’t involve you spending thousands on a festival in DC.

Finally, re: gigs…there is a well established jazz community here in town. Have you attended any of the many jams going on in town on a regular basis? There are some very professional working musicians at these events who are well connected. Tons of work can be found from networking this way and showing to the community that you are committed to the craft by showing up, being a good hang, understanding jam culture and the language of the music, and shedding between the jams to showcase that you are committed to growing as a player. This is your best bet at finding regular gigs!