Wow people here must be really stupid. The original thread was on a student not a full time professional... I don't get why everyone is talking about making it professionally when the kid said he was a high school student. Plus people aren't even answering the poor kids questions except for one or two people.
Anyways... I think what you are doing or planning to do is a great idea and the older generation will definitely enjoy hearing you young artists. They pay may not be what you are expecting but you should get something out of it. You should work it out with the AD of the the specific place you plan to be gigging out at. Also for your size, there may be an issue for spacing so take that into consideration. You set list should be fine because you are "jazz students" so everything there should be taken care of. And never stop trying. You may get rejected from places but don't give up hope!
I wish you the best