I think you are doing very good. Thank you. I took two History of jazz courses in college and those courses were meant as an introduction for the general listener to the jazz music and to give some information on how jazz evolved during the early and mid 20th century. What the lecturer did was to chronologically introduce the major eras in jazz music along with the main performers for each instrument and give some exemplars. After completing the big bands era for example he continued on to the bebop while explaining briefly what was the main determinants for the shift and how individual players responded to it. I felt I should share this because maybe you might want to do something like this. It could make it easier for someone like me to find an initial jazz genre that is more enjoyable and tractable. As someone who had never listened to jazz before taking the courses I now listen to it almost everyday and it was Art Blakey and the Jazz Messengers who caught my attention.
I too have taken two classes on the history of jazz as part of my jazz major. What I've been doing is just posting a variety of tunes (primarily ones I like, to be honest). But I do see how posting tunes in chronological order can be beneficial. I do still have all of my notes from that class so that would help in the "instruction" I'm giving here.