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Well, there seems to be some issue with if the person sending instant messages via Skype is a licensed ham operator, and the role of the control operator vs. the user and it all got complicated very quickly. Not to mention there seemed to be all to much complexity.

That's a shame. The ARES coordinator is the guy I would have gone to. It seems you talked to someone bogged down in bureaucracy, though.

Amateur radio does require licensed operators; I'm not sure this should be a surprise. But the ARES guys in my area are using ham radio for what sounds like the same thing you want. I'll check and see what I can come up with for more information for you. I live in the San Francisco Bay Area, so the hams around here work for Stanford, NASA, Lawrence Livermore, and high tech companies, so I may be spoiled by my resources.

Do you consider yourself in the Philly area or Manhattan? Bucks County can go either way. :-> (I used to live in the Philly area.) Maybe I can put you in touch with more helpful groups.

Although it sounds like you're well on your way to getting things set up, I still suggest having a ham set up for a workaround. This article:
http://www.arrl.org/news/stories/2010/03/03/11371/?nc=1
is clearly slanted in our favor, but it mentions the problems in Haiti in getting their existing infrastructure back on line and how they used amateur radio in the meantime. Note that they used voice via phone patch for comms in some cases. See this video:
http://www.youtube.com/watch?v=JqaKzIkyBug
for an example. And they also used Skype, winlink email, and echolink.