Quoted:
The only way for you to get in is to have your record exspunged. But that will only happen if it was while you were a minor in most cases. I hate to say it but you should have thought about it before doing the crime. Sucks but I gave up/ missed out on that side of life so I didn't screw things up when I was younger.
Stow that advice and save the kid a couple grand in wasted legal fees. An expungement won't do a thing to get him in the military. An ENTNAC will catch it and he will still have to explain the circumstances of the arrests.
OP- what city are you in? A lot of the waiver issue will be very command-specific (i.e.: one recruiting station will write such waivers, others won't). Then again, it is a case-by-case basis even in those stations that write the waivers. Age, ASVAB score, education tier, level of fitness, dependents, etc all enter into the equation.