RocktheCasbah I think there's another implication in that list too: we've generally done well to retain our most important players throughout their best years. Which I think is largely true.
Maybe in retrospect we should have sold a couple of them earlier, but we managed to keep guys like Koscielny for instance, who was easily good enough during a 4-5 year period to play for any team in Europe. We kept Sagna until he was over 30. We kept the Invincibles team together even though everyone predicted they would be chopped up and sold off back in 2003 or so. Thierry stayed for so long, basically an entire career, and didn't end up leaving for sporting reasons.
Even in cases where we've sold players against our will we've mostly come out looking good in the bigger picture. Looking at what we got for guys like Adebayor, Anelka, Hleb, Sanchez and Nasri - and how their careers shook out after leaving - we looked like geniuses.
Cesc is the one we probably should have gotten a lot more for, but transfer fees hadn't really ballooned back then. If he had stayed one or two years more he could have gone for double the amount.