Are you having any particular difficulties with uploading updates, Orange? If there's any trouble with upload speed, you could try uploading a hotfix separate from the main game, with the related .json files. The mod I'm working on, for example, is just little json files, so it's easy for me to upload new updates to itch.io.
If at all possible, you should be uploading new updates continuously, so as to squash known bugs and find out any others.