Can l organize custom shows by month?

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How do you get metadata for this show? That's where the crux of the issue is. Because yes, you could easily organize it manually to be this way, however, automation would be preferable. If you're pulling from a DB, however they have it organized is how you're going to see info pulled into eps on the server. Folder organization plays into it as well, as you could try just throwing things into the folder structure you want manually, seeing what happens with a metadata refresh, and figuring out the automation later.

As for organization -- Jellyfin takes what you have on your disk and serves it without modification, so no, it won't organize it for you. You would need to find a different tool to do this (Servarr, TinyMediaManager, ytdl-sub for YouTube, etc...).