That was one nice broken record, Dev. 
If you would allow me to play my own broken record, I would like to elaborate on Galliani's biggest advantage which is his negotiation skills. Actually, it is a combination of a few factors. See below.
1. He is known to be cheap, and that reputation will help him secure players at a very low price from a desperate/sincere sellers because they know that Galliani would rather walk away and come back the next year than pay a few extra dimes this time; of course if the sellers aren't desperate, then Galliani's such trick would be right away rendered useless.
2. Galliani has a good connection, which is a result of (a) he has been in the trade for long; (b) he usually is respectful, unlike many other colleagues who have a foul mouth or evil heart; ( c) he treats Milan players nicely and treats the reporters nicely too, and of course words spread; (d) he sells cheap, so clubs that have benefited may be grateful, and other clubs would be hopeful too in the future; (e) maybe he has some crazy, under-the-counter deals that make him likeable, that's of course only a speculation, but we have seen several strange deals that otherwise make no financial or athletic sense.
3. Galliani also does possess some quite valuable behind-the-scene strategic skills. Most deals that actually went through were those unexpected by fans or reporters. He seems to enjoy playing with the media and manipulating them to his service, and such unpredictability is part of his good negotiation skills, and of course the most famous case has to be we chased Cannavaro for the entire summer and ended up with Nesta in a last-minute deal. But recent years, he seems to have enjoyed it too much and his success rate has plummeted. Also, I actually wonder maybe it has to do with the increasingly intensified media exposure these days. I know there was internet 10 years back but I don't think every fan knew every move or every potential move, there wasn't tweeter that fanatically followed Galliani and his entourage everywhere, so maybe he was just doing the same thing but now the super-easily accessible, overwhelming information is hurting his game. Galliani thrived with asymmetric information, and it is hard for him to learn the new trick to adapt to this evolving reality (with close-to-perfect information, eventually money talks); or maybe he doesn't want to adapt. I don't blame him for that, but he has to admit that his toolkit is no longer current and eventually, if you can't keep up with the game, you have to quit or you will be thrown out of the game.
Going back to your points, Dev, I think that we all agree that Galliani should see his role reduced to negotiations only, and let other good people have a chance to serve this great club with their talent. But I think we all know the problem: Galliani does not want to share. Galliani felt threatened even when Maldini was still playing for us, let alone now, and that's hurting this club dearly. So he has to go, simple as that.
Another thought (also related to your analysis): instead of buying young players from elsewhere, we can always try to count on our own products. That would greatly reduce the financial risk, as we don't have to pay anyone any money. The first team coach will just work with the primavera coach, promoting a few primavera players by inviting them to train together, and maybe inserting one or two in some insignificant games. If they prove to be good, more chances can be given; not good enough? no harm done, just back to the primavera rank; really good? give them a professional contract and go from there. They usually don't ask for a lot of money either, at least not until they turn out to be great.
Of course, that can be helped if we all use the same formation and similar philosophy in every levels of Milan team, that way, our own youth products can be directly plugged into the first team, as long as they possess good quality instead of having to learn a new system and wither during the process. I believe that Ajax and Barcelona are doing that, and I think we should and can learn from them.
If you would allow me to play my own broken record, I would like to elaborate on Galliani's biggest advantage which is his negotiation skills. Actually, it is a combination of a few factors. See below.
1. He is known to be cheap, and that reputation will help him secure players at a very low price from a desperate/sincere sellers because they know that Galliani would rather walk away and come back the next year than pay a few extra dimes this time; of course if the sellers aren't desperate, then Galliani's such trick would be right away rendered useless.
2. Galliani has a good connection, which is a result of (a) he has been in the trade for long; (b) he usually is respectful, unlike many other colleagues who have a foul mouth or evil heart; ( c) he treats Milan players nicely and treats the reporters nicely too, and of course words spread; (d) he sells cheap, so clubs that have benefited may be grateful, and other clubs would be hopeful too in the future; (e) maybe he has some crazy, under-the-counter deals that make him likeable, that's of course only a speculation, but we have seen several strange deals that otherwise make no financial or athletic sense.
3. Galliani also does possess some quite valuable behind-the-scene strategic skills. Most deals that actually went through were those unexpected by fans or reporters. He seems to enjoy playing with the media and manipulating them to his service, and such unpredictability is part of his good negotiation skills, and of course the most famous case has to be we chased Cannavaro for the entire summer and ended up with Nesta in a last-minute deal. But recent years, he seems to have enjoyed it too much and his success rate has plummeted. Also, I actually wonder maybe it has to do with the increasingly intensified media exposure these days. I know there was internet 10 years back but I don't think every fan knew every move or every potential move, there wasn't tweeter that fanatically followed Galliani and his entourage everywhere, so maybe he was just doing the same thing but now the super-easily accessible, overwhelming information is hurting his game. Galliani thrived with asymmetric information, and it is hard for him to learn the new trick to adapt to this evolving reality (with close-to-perfect information, eventually money talks); or maybe he doesn't want to adapt. I don't blame him for that, but he has to admit that his toolkit is no longer current and eventually, if you can't keep up with the game, you have to quit or you will be thrown out of the game.
Going back to your points, Dev, I think that we all agree that Galliani should see his role reduced to negotiations only, and let other good people have a chance to serve this great club with their talent. But I think we all know the problem: Galliani does not want to share. Galliani felt threatened even when Maldini was still playing for us, let alone now, and that's hurting this club dearly. So he has to go, simple as that.
Another thought (also related to your analysis): instead of buying young players from elsewhere, we can always try to count on our own products. That would greatly reduce the financial risk, as we don't have to pay anyone any money. The first team coach will just work with the primavera coach, promoting a few primavera players by inviting them to train together, and maybe inserting one or two in some insignificant games. If they prove to be good, more chances can be given; not good enough? no harm done, just back to the primavera rank; really good? give them a professional contract and go from there. They usually don't ask for a lot of money either, at least not until they turn out to be great.
Of course, that can be helped if we all use the same formation and similar philosophy in every levels of Milan team, that way, our own youth products can be directly plugged into the first team, as long as they possess good quality instead of having to learn a new system and wither during the process. I believe that Ajax and Barcelona are doing that, and I think we should and can learn from them.
