In fairness calderwood was given some money to spend on transfer fee's, the club had a bigger wage budget due to higher attendances and a better tv deal, the global recession hadn't started yet and in general the football on the park across the spl was of a higher standard (not by much i grant you).
I blame the demise of calderwood on milne for not backing him financially after the copenhagen game. If we had strengthened then with a couple of players rather than punting clark and hart for meagre fee's i think we would have continued to improve under that regime. The club went into decline after we went out of europe after steady progression previously. Going out of cups 3 years running to lower league opposition put pay to JC and that was that. I found it harsh that he was sacked after getting us into europe but i wasn't gutted he was leaving, at the time i was still fucking raging with him for sucking up kyle laffertys ass after the game he screwed us at ibrox. "charlies come off saying he's no touched him and charlies an honest player but..... ya know..... big kyle he's an honest player too" Whatever can be said about JC i still find it interesting that no-ones offered him more than 6 month contracts ever since.
Scottish football is totally fucked. The problems we face are all down to the shocking financial climate that the league has developed. Milne has made many mistakes but the biggest i feel is that as chairmen of one of the biggest clubs in scotland he has not rallied the chairmen of utd, hearts, hibs, motherwell etc etc to stand up to the old firm. They are the biggest problem with our game. Two giant parasites that are..... no actually have sucked all the life out of scottish football. The laying down to their demands of 11-1 voting when the spl was formed was the first step to the road to oblivion. Its been 26 years since we won the league and no one outside the O/F has won it since. Its no wonder folk are turning away in droves, the product is piss poor, the best you have to aim for is 3rd and even if you manage that you're probably going to get horsed out of europe in august anyway.
There are of course other factors like the saturation coverage of the epl which has helped the decline of interest in going to games but this has added to the effect rather than causing it. Scottish football needs to start afresh. Scrap the 3 ruling bodies and start again. A good league to take inspiration from would be the bundesliga imo