I found a bug on that page: a sentence that says "Microsoft has sole discretion etc" is repeated twice. (Search on discretion.) How much does that go for?

Would love to know from those with experience if a bug/exploit is worth more when declared through official channels or 'unofficial' channels?

I'm sure the max payout for going black hat is higher. But not going to jail and still getting paid is good too.

Depends on many things... but realistically if you're at a point with which you can ask that question, you'll already know your answer.