I don't think being at the lower end of the playoff bracket is the worst place to be. I disagree with the principle that you should either be the best team in the league or else utter shit for the draft pick, otherwise you're wasting your time. However, I think being at the lower end of the playoff bracket and being capped out all the way up to the luxury tax line is pretty close to the worst place to be. That's why I think Olshey needs to go. It's one thing to have a mediocre roster--it's quite another to be paying through the nose for a mediocre roster.
Why would you expect guys to make a big leap simply because they got a big contract? You have to assume they were already working hard last year to get the contract. Where do you go from there other than gradual improvement at best? You might be frustrated by that, but if Stotts and Olshey are, they don't understand the game and sports psychology well enough to be in their positions. Generally speaking, contracts are what the player figures to be worth mid to late in the deal, not first year.