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My answer to your question
The obvious answer to your question (Where do you find...?) is - you need to find a "digital native." As you may know, "digital natives" (according to Marc Prensky) are those who were born into this new digital world. Simply put, NPOs need to enlist the services of young people in their mission. And that is a whole other conversation...
The other answer (here is my opportunity for the soap box): Yes, there needs to be easier applications to accomplish these tasks. Regretfully this will probably come when the commerical software developers catch up with the open source people and create commercial apps that do the same things. I am waiting for "Microsoft's Blog Creator" to appear any moment. Don't expect this any time soon.
But seriously, most of the open source stuff is always going to be on the edge and expect that the user has some tech saavy. It is the nature of the beast.
I too went through a very recent experience, similar to you own, in which I installed Moodle on my host web server. I held my breath hoping I was not crashing every server between Maine and Florida. But it did work and my confidence level has risen (I did this with only a little support from my hosting company).
All this said, you also need to realize that the notion of Web 2.0 is a philosophy and not a technology. Web 2.0 is about using technology in the creation of new communities, it is not about the toys, it's about the people. So, in some ways, don't sweat the technology issues - find some native who likes to play with these toys and have them do that tech stuff for you. You should put your energy into using the technology to enhance and create the communities that will help your mission or help you achieve your mission.
John Brandt Executive Director Maine ASCD info@maineascd.org www.maineascd.org