Please feel free to suggest reading and to give directions, because your knowledge is undoubtedly more thorough than mine.
I mainly rely on studies and bibliography from the defunct AIH (Italian Haiku Association), of which I was a member.
In past editions of Mizu no Oto I have written some small and rough articles aimed at beginners - one of them even talked about titles in haiku - however from a mostly classical perspective.
What little I know about the gendai movement comes mostly from Richard Gilbert's studies.
Regarding Takahama Kyoshi, I talked about him in one of the last articles, but unfortunately in unflattering terms, having been associated with the reaction against the period of experimentation that arose from other students of Masaoka Shiki and being associated with the conservative motto kachofuei, which although allowed us to keep the founding principles of haiku up to the present day, was also rather reductive.
However, feel free to intervene and also to participate ... we need both spontaneity and theoretical preparation.
@bananafish - I'll have to go look up your article on Kyoshi after I write this. We would probably agree about him. His haiku are about average, I think. Some bad, some fantastic, most just average. But it is his politics and his ironfisted attempts at control of the haiku world that makes me dislike him.
Gilbert's work on the gender movement are really the best you will find in English. He has done fantastic and amazing work. If you've read his writing, you are ahead of the game.
I am a huge fan of the two shinkeikō students of Ogiwara: Santōka and Hosai. I am currently, in fact, along with a Japanese colleague working on a book of translations and history for both men. Although I of course enjoy Bashō, Buson, and others of the bigger names (and if you look up my past translations on Hive, those names fill most of whom I have translated), it is those two free-verse haiku poets to which I always return.
Are you Italian, then? My father is Sicilian. His father's family was from Sicily for generations and his mother was from Bari.