Not unintuitive, but thinking about it from a beginner standpoint, calamares-based systems are way easier to ‘get’. These distros don’t ask for domain names, proxies, usage surveys etc. This stuff isn’t that complicated, but they add an extra level of things you need to worry about if you’ve never used Linux before, which is the kind of person who this flow chart is made for.
I never see toffeeshare mentioned. P2P, encrypted, no size limit. Only problem is you can’t send folders, only files, but that’s easily solved with tarballs or RARs.