I was brought up differently, to be ambitious, strive for better things, look at the people above and say "why cant we be more like them". Why shouldnt we strive to be a better team? Because of what happened to Leeds? Why live in fear like that. Nobody is saying that we needed to go out and spend 5x£30m on Rooney level players. But a little bit of speculate to accumulate would have been a good risk to take.
Football is a cyclical game, we had the opportunity with spending a little more money at the right times to take ourselves forwards, 2008 being a prime example where we chose to stick rather than twist and it cost us the league. When we have been in a position where we had good players, for example Nasri and Fabregas, we chose not to strengthen, but to stick, and rely on them with no quality in reserve, rather than to spend the extra £10m and bring in (eg) Arteta and Reina when the squad really would have benefitted from it.
Thats what annoys me the most, missed opportunity.