1-Is sports betting over the internet illegal? I live in New Jersey and have heard conflicting reports.
2-I also heard that it isn't illegal but it is illegal for US banks to transfer money to internet gambling sites, if you want to bet you have to use an intermediate. Is this true? If so what type of intermediate should you use?
3-If you win money will you have a tough time cashing it in? And should you report it to get taxed by the government?
4-If Internet betting is illegal what is the penalty?
2-I also heard that it isn't illegal but it is illegal for US banks to transfer money to internet gambling sites, if you want to bet you have to use an intermediate. Is this true? If so what type of intermediate should you use?
3-If you win money will you have a tough time cashing it in? And should you report it to get taxed by the government?
4-If Internet betting is illegal what is the penalty?

and that is not good for you.. 
I too, have had a few times where they don't ask for any ID or anything around $1K. Like you said, most of time, no questions asked, but there are a few times when they do... Not that it really matters giving your ID or even your SS#...