Ywn use a piece of software as comfy as freenet again

Hmm, I don't think so.
The average citizen didn't even really used the internet 15 years ago, at most they just read news, emails and chatted on ICQ or on shitty chat websites that existed at the time.
The average geek/nerd demographic who did knew how to FTP and stuff did not care but the average normie do care and get utterly triggered and butthurt just at the thought of it.

There is not much to get into. It's not more anonymous than its underlying network connection.

I think you confuse it with '80s and '90s. I don't know where you're from, but in my country years 2000-2007 are the years of computer boom, stashes of CD-Rs, amateur LANs, and, in later years, the exponential spread of fixed interned connectivity.

Modern IT startup stereotype implies catering to lazy uneducated masses is the only possible way (obviously, that's a complete lie). Because of it, you believe people who managed to run a filesharing client or burn a CD-R must had been "geeky". They were just random people who had a computer. I don't mean all of them tolerated child porn, or even seen it, but it was not treated differently in general. Then law enforcement caught up with the times and sent signals to admins of all kinds that everyone who doesn't have an anti-CP policy will get their attention (the same had happened across shady strata of World Wide Web a couple of years earlier). The problem was glossed over with minimum amount of work, something that had been in clear sight the day before became underground, and concerned grannies would not find anything like that on accident anymore.

You also confuse public socially acceptable behavior with what people actually do privately. Satirizing "think of the children" mentality is hard, not many do that. At the same time, most people (male) who watch e. g. Galitsin videos fap first and ask questions about age later.

That's actually how it works most of the time. Freenet use or running a tor exit node etc. establishes suspicion allegedly "beyond reasonable doubt", the hick town county judge signs a search warrant, and then the good boys get to don their M4s and dress up in swat gear to kick down a door at 4AM. You better have your drives encrypted and offline when that happens even if you're innocent, because they'll happily plant what they need to find.

No, in last years people have been caught while actively working with monitored software and having encrypted storage mount.