That is a completely fair point. What is the difference?
I see it as 'who is being scammed' and what is the harm done.
Now in the kid's case he did use AOL resources which, had he not, they would have been used on AOL employees (thinking mostly food here, the energy/light/water usage is probably flat rate like it is in my facilities). He did not do monetary damage to AOL, nor reputational damage (he didn't represent his work as being part of AOL or represent himself as an AOL representative to potential partners or investors).
In Shirley's case she allegedly convinced some people she would be able to connect them with potential investors or advisers when in fact she could not. For a startup founder that can make them think there is some additional outreach going on that isn't. If the founder feels like outreach is critical to the startups ability to succeed and they find they have squandered time, their most precious resource, with this person who couldn't deliver then I could see them feel betrayed. If you hire (and pay) a PR firm to get your message out and they say they can get you into the New York Times or Inc or whatever and it turns out they can't and never could, you may be inclined to not pay them (and possibly sue them if you had already paid them).
So one is 'freeloading' (the kids case) and one is fraud (Shirley's case). I see it as the difference between saying you have a million dollars in your checking account when you don't, versus writing a check for a million dollars when you don't have it. Shopping yourself into photos feels more like the latter to me, but unless you're actually paying for her services your not financially harmed.
I think asking the hypocrisy question is completely valid. Where does this behavior cross the line from 'white lie' into 'fraud'?
In my post I really was commenting on people trying suppress conversation that is painful through peer pressure. Conflict avoidance is a huge problem in society, it lets problems grow into bigger problems. I was not particularly passing judgement on Shirley's actions, although in all honestly when I read the TC article I did feel sympathy for the folks who were misled, and I didn't feel nearly as much angst for the AOL folks who didn't realize the guy was living in their office.
The kid's motivations were pretty clear, do you happen to have any insights into Shirleys? I'll admit I accepted the implication that she does this just to prop up her own self image, but recognize that conclusion isn't completely supported by what we know. Motive does play a huge part in how the two stories get positioned.
(This comes back to my comment in that previous thread : When evaluating a series of events involving grey areas its always useful to try to understand the principles that are in play. Different sets of principles would lead you down two different paths.)