So, the first problem is that of the taxman. barter networks have a long history, and courts have consistently ruled that barter doesn't excuse you from paying taxes. If you get big, they /will/ come after you.
I'm not a lawyer, and you'd need to talk to one. But my belief is that if it operated like the current systems, where helping people got you an informal 'reputation boost' and people with good reputations are more likely to get help when they ask for it, the irs wouldn't come after you, because it looks very different from any kind of economic exchange.
Now, I don't know how far you could take the reputation points. could you make actual tradeable carma? would the irs come then? I'm not a lawyer, I don't know. But I'm pretty sure that if you stick to the existing carma/reputation type systems where you get points, formally or informally for helping people, they won't come after you.
eh, I think building cultural norms (and a way of 'keeping score' without being so formal as to arouse the ire of the IRS.) is more important than the technical problem of matching claimed skills.
I think the problem is partially solved by public mailing lists, or things like stackoverflow... people gain a certain reputation. and when someone with a good reputation asks for help, they're more likely to get it.
The problem with all current systems is that they are very focused on one niche. you have your SysAdmin lists, your programmer lists, your designer lists, etc... and a good reputation on one does not always carry to others, which is what needs to happen. I want to, say, give some SysAdmin advice/help and get some design advice/help.
So how would we start an 'open help community' for a wider audience? a community with both SysAdmins and Designers, for instance?
at that point, you have a bigger problem with reputation. Lots of people will give you advice outside of their area of expertise. For instance, I'm a pretty good sysadmin, at least when you care about money. But I'm happy to also ladle out business advice, an area where I have a pretty trivial amount of experience, and not very much success. And look at this post! I'm handing out legal advice, even though I'm wholly unqualified to do that.
Your reputation system needs to be able to deal with that. Another complication is that informal reputations work really well on narrow focus lists. usually 'it takes one to known one.' - I don't know a good design when I see it. The vary thing that makes me bad at design makes it impossible for me to recognize a good designer. But I can spot a good sysadmin from a mile out. It's easy for me to tell between good sysadmin advice and bad sysadmin advice, even if the advice is somewhat above my level. I can tell if it "sounds right" and I know how to verify.