If you are using windows, then you should definitely try out WinAutomation. This software combines the capabilities of all the "flavors" that you mentioned while retaining an easy-to-use and intuitive interface. WinAutomation can handle web tasks (e.g. scraping), excel automation, interact with databases, schedule tasks or call them via triggers and it is the only software I know that can handle Windows UI automation.
I was also using different languages/methods depending on the task at hand, but this ultimately required more work than I was willing to put into automating. To be honest, I liked the software so much that once I found out that it is made by a small company in my country I applied for a job there and got hired :)
In my opinion, WinAutomation is much better than all these "well-known" software that OP mentioned, for both the average, as well as the power user due to its simplicity. Don't take my word for it though, there is a 30-day trial on the site and many sample scripts on the forums. I am pretty sure that the development team would love having some feedback from reddit!
Edit: We got a lot of requests for a discount coupon for redditors, so here you go: Use coupon WAREDDITNOW in our purchase page.
I am sorry I didn't see this conversation earlier. I think that establishing a trusted network similar this could be done much more easily than that, assuming that the f2f/p2p connection can be used to bridge or connect groups of people who are connected by more than one degree of separation. It's not that difficult to crank out simple html/javascript based facebook and mobile apps that invite your contacts to join the network. I have an Android app called Droidin that allows me to consolidate my Google and LinkedIn contact lists, so it should be relatively simple to clone that functionality. Once people agree to join the network (and consolidate their contacts into one list) they can move from the app to a (link to a...) Winautomation or Autoit script that automates the configuration of their network on their Windows PC. Those are the windows-only tools I am familiar with, so at least in my case that's what I have in mind for promoting the darknet. With all of the programmers we have volunteering for this project, I'm sure that once they see how these automation scripts work they could easily code setup-automation scripts for platforms other than Windows and Android.
~~You can use keyboard and mouse automation. I only tried commercial ones like this: https://www.jitbit.com/macro-recorder/ or http://www.winautomation.com/ but there should be ones also or you can write a program in C#/Java relatively fast too.~~ Sorry, forgot you have to read the data too.