First off
Second he does make a couple of good points.. First about the arrogance...In popular culture there is a notion that if you're rich you must be doing everything right...N1ggas like Kanye pick up on the insecurity of his fanbase and knows he could do whatever he wants to troll them..What are they gonna say? He's rich and popular.. So he MUST be making the right moves..That's a powerful position to have and you can use that influence to take your minions anywhere for your amusement..
He's built up a resume for that influence.. If he would have wore a skirt on the cover of College Dropout he wouldn't have been legitamized...It probably would have been his first and last album...
Also his point about physical emasculation for the purpose of making white people feel more comfortable is something I never thought of.. And actually much more sinister than just doing it for the sake of attention whoring..
Lastly
Nobody that he's addressing knows who Lord Jamar is and is gonna care about what he has to say on the issue...