I asked this question a while ago, not sure either whether it is a good strategy or not (production-wise). For sure, it's a well-known cognitive effect that breaking a big job like an entire update into smaller tasks often gives you a more sense of accomplishment because the "reward", even if smaller, comes earlier. And I'm not talking about us the readers/players, but for the developer: it could be a more satisfying and less boring and wearing way to work if you see the result of your work coming live quicker. It's a very general concept and it also depends on the person, some like this way better than the other. I don't think it's the (main) reason for this change but it's probably a factor to take into account as well.
Concerning the connectivity between events, yes you are right and it is a risk. On the other hand, I find kind of difficult to find past events that were somehow linked together, other than some few lines in the dialogue, often optional based on the choices of the previous event (e.g. in the last update Sophia thinking that it was the x-th time that somebody saw her breasts that day, with x different according previous choices).
We often said in the forum that, on the contrary, Sophia seems to "reset" after each event, which from a development point of view it's easier because you don't have to branch too much the dialogues and stories. But I see your point that this update strategy can exacerbate this particular feeling story-wise and in the development of the character.
My other concern, since I always keep an eye to the renpy script, is that this strategy could be difficult to manage when you have multiple events in parallel or optional. In the last update, Emma's event, the dressing and the task were kind of intertwined, some being mutually exclusive, some sharing some common script/renders etc. What I'm saying is that it could be more difficult to check for bugs and plothole if each event is treated separately but they are somehow related. I mean it's not a big big issue, but for sure it could be one of the drawbacks of switching to this strategy.
And of course I agree that it does not solve the original problem about the development cycle. It could have an impact for what I said above in that he could be more "engaged" with the production but it won't solve the whole problem.
