I performed some research on filesharing and anonimity, but it turns out anything I read is not about what I need.
Most articles and forums recommend not to use services like Google Drive or Dropbox, as they don't run on opensource code so you really need to trust the software to be sure your data is safe. Fair enough, but that is not what I need.
I don't care if the data is safe or not, I just need seamless file sharing, that anybody in the "normal web" can use without having to install complicated software, without ever having to do with command lines etc. I want them to use something mainstream and uncomplicated.
I'd connect to the filesharing website via TAILS, and I don't want any of my data (eg IP, DNS, ISP, MAC, approximate location... you name it) to be compromised by this setup.
Of course I'll need to pay much attention to the metadata, to avoid giving away information. But what I'm concerned about is the possibility for the filesharing platform to trace me down through their fancy java functionalities or other tool that may compromise anonimity even if I use TAILS.
Today for example I was testing Dropbox.
To my big surprise they do allow TAILS users with some very limited captcha checks and double factor email authentication.
The point is, I have no chance to see their log and check where do they think I am from. That's why I'm here asking the experts.
So, to cut a long story short: what would be your best advice to share files and folders with non-anonymous users while staying anonymous, and having them performing all the routine activities they usually perform with filesharing?
After Dropbox, here's my checklist (I haven't visited any of them yet):