With just barely glancing at the output you posted it looks legit.
Best advice i think .. or maybe not best, however its what i would do. Is to join to the router either with windows or nix and pcap it. The switch your mac clear the dhcp lease and pcap it again. Then compare those 2 against the one your program outputs that doesn't work. So that in the end your program exactly mimics the working leases you got. Once you have that, you can go back in and "fuzz" around with the dhcp option codes and see what works and what doesn't.
Hope that was of some help, altho i probably missed the point entirely
edit: If your having to auth to the wifi then yes you need to "pretty sure atleast" reauth for each lease that you grab if your clearing it first .. you could always request another tho without switching the mac. I could be over thinking it ... but it does sound like a nifty little experiment.