Graphic designers, lend me your ears, and opinions

Right now I work as the art director for a small, locally published but nationally distributed jazz magazine. This morning I got a call from a guy who used to be one of our editors, who is now living in Pennsylvania. He has a mind to start his own local rag, along the same lines, content-wise, as The New Yorker, but for his locale. He called me for some info on how long it takes me to do my job, what’s needed, basically just picking my brain. But the conversation slid towards the possibility of my actually doing to job for him myself, from here. I certainly have the time after-hours, that doesn’t concern me.

But the long-distance thing does, somewhat. I’ve never done a graphic-design project long-distance like that, and I wonder what kinds of hurdles I might run into if I were to take the job on. Anyone have any anecdotes about doing such a thing that they’d like to share? Anyone know of any resources, either online or software, that would help in doing a job like this?

Thanks in advance for any help.

I am a creative director and I work 100% from home, both fulltime for a CA company and freelance for companies all over. The number 1 issue with working remotely is: you will be out of the loop. Many decisions are made with random chitchat while getting coffee or just dropping by someone’s office, and you won’t be in on that. Make sure you are in some sort of weekly meeting that goes over not only your projects but everything that’s going on and being planned. And see if you can get everyone on instant messenger, it is helpful for the kind of quick questions you’d normally stop by someone’s desk to ask. If you are working afterhours, it will be trickier since the people you want to talk to may very well be gone for the day, which delays things dramatically. If you will be the art director, will you have to supervise people who are working regular hours while you work only afterhours?

No, it’ll just be me on the creative side (as it is now in my real day job, I do everything myself). Pretty much the same for the guy who’s going to be publishing. He’s planning on doing most of the work himself, which I think is going to be a hell of a lot of work, but it’s his gig. So I’d really only be working with him, and I don’t think communication would be much of a problem. My current job is flexible enough that I can take calls, deal with other things, or even leave the office if necessary, as long as I get things done on time.

The random chitchat thing is one aspect that actually bothers him. He likes the face to face back-and-forth thing, and isn’t sure he’d be able to work with someone that’s not within visiting distance.