I don't think the Board "got their sums wrong" - when we were all up in arms about the new Rangers staying the the top flight, they presented a worst case scenario of the financials to show how it would impact the club. As Brazilian said, there were already sunk costs prior to the vote, so a loss that season was inevitable.
Then the prize money was changed, and on top of that, no league sponsor has also robbed us of some funds. Then we had the bad luck of a Euro tie that probably ended up costing us some money, plus a dire Cup record this year that I doubt we could have predicted.
Under these circumstances, we have cut our wage bill and still managed to put a competitive team on the park.
As for the Society itself, I don't think anyone was expecting to raise 1.5 million from just the fans. The first push rasied close to half a million, and I'm sure subsequent drives could bump that up towards 50% or so of the target. Where it has failed is in attracting many business level investors. Without those, it was always going to be a big ask.
So, for me, the big question is what can we do to get companies (or owners of those companies) to invest in the Society at higher levels. I don't think there is a simple answer, but it's something we really need to focus on in the coming months.