Yeah I would agree that the progress bar was not one of the most well thought out things the dev has done, considering he has ended up having to make multiple posts since just to explain it's status.
I disagree, it was quite well-thought out to keep the patreons in line. I am quite sure that the update is already finished, he simply needs some days to cash in the patreons for another month.
That might sound cynical, but for months patrons and pirates alike hear the same sermon over and over, how unexpectedly something popped up. that might happen once or twice but not this often. It cannot have escaped gumdrop that anywhere his game pops up, it is mentioned that he works as fast as a tranquilized Faultier. So, he should know to start earlier to make the next update. But personally, I do not believe his being in over the head story any longer.
I am an author myself and while I do not take money, I am able to keep up a schedule of updating once or twice a month despite health concerns and a full real life calendar.
(OK, writing is not quite as time-consuming as rendering a ton of pictures, but it is not as if gumdrop has no measure how long it takes. As said, at first, underestimating rendertime is possible, but months into work he simply must konw how long an update approximately will take)