The Pitmaster does not have food probes. I think the higher end Guru's can be fitted for multiple food probes, but not sure. I think you need to go with the Stoker. I personally do not have one, but they can accomodate multiple food probes and I believe there is a program for Macs. The stoker is a bit more expensive than the others.
I do have a guru and love it. I didn't need or want the extra features that the Stoker offered, although it is pretty cool to remotely control pit temps and monitor food temps from your iphone.
Bubba Keg / Stumps Baby / Super Fast Yellow Thermapen / Lodge Cast Iron Grill / Smoke Vault