PKA,
You are getting great information from everyone. But, I will try one more time to say SLOW down.
I am not a networking genius (networking can be a huge headache sometimes as troubleshooting is not always easy). It took me over two months to design my network including purchasing hardware and software. It seems you are trying to do it overnight. Just my observation. My sincere apologies if I am wrong.
If you are looking to connect satellite offices, then you may want to rethink wireless at the satellite offices. You can wire rented space. You may wish to consider VoIP as one of the biggest advantages of VoIP is that phones in your satellite will be like extensions of your phones in your main office. If you have Internet and Ethernet, you will have VoIP. And, you can take a VoIP phone on a conference to Japan or to your house and have local service with the same phone number.
Are you truly researching your OS? If you were and you are hiring an IT person, why not go with SBS 2008? A little silly to start fresh with an OS that is five years old when you have an IT person to set up 2008. Of course, it is 64 bit. Make sure AC is compatible.
Last time I checked there are two Vista Businesses. One is Vista Business-N. I could be wrong there.
Most networkable fax machines (MFPs) come with the software for PC to Fax. You can go with Brother at around $500 or more or go with Xerox or Toshiba at $7,000.00. As you said, you get what you pay for.
Scansnap is for scanning not faxing. TWAIN, while OK, isn't really necessary although it can be helpful. Took me and Adam over a month to research MFP and I ended up with four models, before I was happy with Xerox.
LogMeIn is great to remote into a computer to work on it but would absolutely not be a solution for connecting offices. There are other solutions. As you said, you will need IT? Who will you get? You may want to make sure they are SBS Certified with Microsoft.
iPhone is a good phone. I do believe it can work with Exchange Server. Or do you want to go with tried and true Blackberry with BES? Or use Windows 6.1? All things to research. Are you going to trust your entire office to a cell phone or am I reading that wrong? VoIP and OneBox and iPhone, etc. is great but sometimes good old POTS digital is the way to start off. You need a fax line and sometimes you will want a backup regular phone line anyway. There are phone companies which will set you up with both.
This is my last please. Please take you time and research things more. OneBox is great, but I wouldn't jump to it, because it works for Adam. Look at VMail, etc.