The content for all of the updates this year so far had actually been planned by Ranli since January. He posted a schedule back then with descriptions for all of them up to June.
So far, he hasn't actually deviated much from the plans. The March and April updates ended up combined in the end, and the May update included Chad's dream instead of Cici's, probably so that there would be both Gay and Straight content for the update.
He hasn't developed any original Holodeck missions so far, which is a shame, as I think this is one of the main reasons why the 2nd season feels so empty and content-less so far. He had introduced so many characters to interact with, but most of the missions right now are by guest writers that promote their own games and characters. The February update was probably the only really "solid" update so far because it actually utilized the original characters and had them interacting.
I have pretty mixed feelings about the overall pace of the development. While clearly it allows for consistent updates that are (mostly) on schedule, it is kind of ridiculous when you think about it - it has taken half a year to create one in-game day. At this rate the game won't be finished in a reasonable amount of time. On the other hand, this is a one-man project, and I wouldn't pretend to know how time-consuming and exhausting game development is. Ranli seems to have found a pace that works for him, and it's probably better than having the updates come out months apart, like with the bunk updates, but, imo, I still want them to have a bit more substance to them.