It seems like the new idea you're adding to the forum is that local EA groups should earn money together.
My gut reaction is that freelancing with a rotating group that's open to anyone would be an inefficient way of making money. Normally, the process of applying for jobs takes a while, so you'd really have to know in advance who's going to be attending the meet-up and what skills they have.
You might solve this by always taking the same type of jobs--maybe you always work in HTML because it's easy. But easy jobs won't pay well. You'll be competing with developers in very poor countries.
Another way to solve it could be to create a small business with a few talented EA friends and plan to donate the profits (cf Founder's Pledge). That way you could expect commitment, know skillsets in advance, and don't have a revolving door of people to teach. You'll be able to take on more challenging, specialized jobs that will pay you more. I'm not sure Upwork is the best place to find those jobs, but if you have technically talented and altruistic friends, maybe freelancing or starting a business is a good idea.
For most of us, I think a better way to have impact is to improve our performance at our day job. Getting a raise/bonus/promotion will almost definitely be worth more than freelancing. For some people, improving their performance at their day job means learning something new; those people might want to start a reading or study group together (EA London has a few). For other people, improving their work performance comes down to putting in the hours at work, and what they need from EA events is a place to socialize and be reminded why they do what they do.
I don't think the idea of freelancing together is a bad one, I just think it's not the optimal use of groups' time. Let me know if you disagree with anything I've said. - Kirsten
EDIT: Improving their performance at their day jobs will often also be a way for people doing direct work to have impact, even if they don't get paid extra.

I would encourage the friend to take a longer-term view to see the value in discussing ideas.
I would also encourage the friend to try out doing the direct-work meetup concept. I suspect there are good reasons why that style meetup is not popular, but would be delighted to see them pioneer it successfully.
The following EA Forum post may be relevant to you. I'm not sure how Madison vs Harvard differ, though I suspect they are both more similar to each other than they are to the contract-work-and-donate model of an EA meetup you are conceptualizing: http://effective-altruism.com/ea/1nh/heuristics_from_running_harvard_and_oxford_ea/
Some value I see in the social discussion style EA meetups I am familiar with (I co-organize EA Austin and have been to Chicago a couple times):
Prevent value drift through facilitating the development of friendships and closer ties between community members
Inform EA community members about new ideas which they can then go home and read further about online (high fidelity learning)
Have more personalized discussions about career planning than is easy/typical in online EA discussions