relax guys, we're all here to talk about football. No need to get all upset!!!
There are a few reasons why Ajax has a kick ass young team and Milan doesnt. Firstly, Milan is in a huge soccer market where it is very important for the management to see that the team is always great and is in the top 3-4 teams each year due to the TV revenues and the importance of AC Milan for Berlusconi's media empire. So Milan can't afford to spend time developing young players like Ajax. If they suck for a couple of years, the revenue loss from TV etc. is too great. So they always buy the best from other teams. Sorta the same strategy that NY Yankees, Real Madrid, Man U use since they're also huge TV market teams.
The second is the size of the Italian league. There are teams in each and every corner of Italy and the competition to recruit the best players in each region is so high that it's difficult for Milan to obtain the best young players within Italy. If you're a promising youngster in Italy, there are so many big teams like Milan, Juve, Inter, Roma that will try to grab you. And a lot of players who have loyalties to their regional team wind up wanting to play for them. Ajax on the other hand is the only big name Dutch team and playing for Ajax is the best way to make sure you'll get your career on the fast track. That is why it's easy for Ajax to attract all the good youngsters in Holland to join them.
The other Interesting little note is that many of your foriegn players are of Surinamese origin. For them, all their heroes from back home seem to have played for Ajax. (Rijkaard, Kluivert, Winter, Davids, Seedorf etc.) The only exception was Gullit who played for Den Haague. So if you're a young Surinamese player, the team to play for is Ajax so it's so much easier for Ajax to get the foriegn players.
You are right on the money about the boseman transfers 'cos that makes small market teams like Ajax lose their top players to the big boys in Europe. This sadly will not change since Football is big business and the big teams will pay whatever they have to get the players they want. Holland is not the only country suffering from this. Look at Brazil where the top players all want to play in la Liga or Serie A or from recently in the Premier League.
If you think Ajax is getting screwed by big teams like Milan, Man U, Real etc buying your top players, just think of how the other Dutch teams think of Ajax. I bet they look at Ajax the same way you look at Milan 'cos in Holland, Ajax is the king of the hill and you get the best players. But in Europe, Ajax is a small team so they then face the same problems with bigger teams from other countries!!!