It seems that every new season the amount listed of available cash for hiring staff is not being displayed accurately, which I think is the cause of a lot of frustration and confusion for a lot of people, myself included.

Could you give an example of what you're seeing exactly?

L9 just rolled over to a new season. It's currently showing that I am already OVER my allocated money with just over $14M spent. This is something I've experienced with all of my teams, where it declares that I'm going over my cash flow when offering new contracts, but then still allows them to get through. Later in the season, for some reason it'll adjust and show the 'true' cash flow I had available. For instance, in L8 it kept showing me as over, but then after a week or so it suddenly 'fixed' and now shows me as more than $10M under cap, which would have been awesome to know as I was bidding (and losing) on contracts.

I have noticed this as well but only at the season turn. It corrects the next day.