Well, a good idea would be that trojan idea if used properly...first of all if he has an AV it will most likely detect this trojan, although if he doesn't you can set it to auto-start on a CD-ROM (don't know exactly how) then you pop in the CD while he isn't looking then when he isn't looking again take it back out then try to disable the firewall or install a keylogger might get something usefull out of it. The LC4 idea is really good as well as the idea to slow your port scanner speed down a bit. Look for some security bugs and pray that he hasn't already patched them :P Social Engineering would be your best bet. Can't think of any good ideas at the moment. How long does this challenge last?