Okay, so I was browsing around for solutions for OS X to connect to a bluetooth cellphone, when I thought: "hey, I have a GSM phone. Why not just get a cellphone radio, and drop my SIM in there?" I already iSync my hiptop to my computer, so all of my contacts are in there. I googled around and found this module, and looks really really cool
GSM Module. It looks simple enough to interface with (assuming you know how to interface w/ the serial port, and you knew how to program), since its just simple serial commands (to place a call: send the command ATD 3035551234 and it'll dial it). Of course, you'll have to program in things like entering in a SIM password, and signal strength meter, but otherwise it should be relatively simple. Plus since Tiger can use a bluetooth headset for audio input, you should be fine. An added bonus is that you can use a higher-gain antenna to get better reception, and the site also sells integrated GSM/GPS antennas, so you only have to mount one plastic lump on your car/roof.
Sorry, no version for CDMA people, like Verizon or Sprint. Nextel has OEM modules, but they're probably insanely difficult to program. Random rambling: WHY DID VERIZON USE A NETWORK STANDARD DIFFERENT FROM THE REST OF THE WORLD?????? (yes, I know Japan uses its own crazy standard, but they've also got toilets that are robotic and other fancy stuff.)