Lots to think about here. Thanks for asking the tough questions, Sinem!
I used to create a newsletter for a community music group, and it was pretty much a one-man show. More often than not, it was like pulling teeth to get more than a few members of the group to contribute.
As much as I'm intrigued by the joint-paid-newsletter idea, I fear it would be more trouble than it's worth if I can't find folks who 1) are interested in the same topics I am and 2) are willing to commit to writing something, say, once a month.
And like you say, I don't have enough willing-to-pay fans to make it worth my time...yet. The journey continues.