I'll take address all three issues:
1) What the guy does with the cash after you give it to him is his business.
2) I was (sorta) joking with the property management companies and the documentation. But if you don't have the documentation they request, your options are either not tell the whole truth or find another place.
3) As for the contract issue, that's entirely a civil matter. I assure you that the big property management companies don't care whether you walk out on the lease nor will they miss your money. So don't feel obligated to sit there and break your back just to pay a lease. As I stated at the beginning, the best rental deals are those that don't require a lease at all.