Boku no Natsuyasumi video came out on 9-25 last year. It's feels semiplausible that it's going to be a surprise drop of a video and it will be announced that the following videos will be released on a more regular schedule like every 2 or 3 months.
Just saying- wild speculation, but I have been missing me some Action Button goodness.
devtesla wrote
Tim's only social media at this point is a once a week Friday twitch stream, and he said during a stream that that's where he's gonna announce future videos, by saying something like "new video coming the Sunday after next". No other promotion than that, Lol. And yeah it'll specifically be on a Sunday and announced on the Friday 9 days before. So the earliest we'll get a video is October 1st but like don't count on it Lol.
The Boku no Natsuyasumi video was a level of effort about what you would expect for a feature documentary, so unless he reduces scope by a lot then don't expect a regular release schedule.