Your thesis implies that before using my data I am compelled by law to know very well the terms of use; I think the opposite has happened in practice, especially in Europe the trend is to say that lengthy TOS don't mean that companies can do whatever they want/ just because the end-user clicked "I agree" doesn't automatically make them liable, in the eyes of the law, to know and understand all implications of the TOS. That's undue burden.
I guess you can argue that "I should've known that OpenAI will use my conversations if I send them to ChatGPT" but I'm not convinced it'd be crystal clear in court that I'm liable. Like I said.... I think until actually litigated, this is very much a gray area.
P.S. The distinction you make between "properly secured" and "improperly secured" nextcloud instance would, again, be a legal nightmare. I guess there could be an example of "criminal negligence" in extreme cases, but given companies get hacked all the time (more often than not with relatively minor consequences), and even Troy Hunt was hacked(https://www.troyhunt.com/a-sneaky-phish-just-grabbed-my-mail...) - I have a hard time believing the average Joe would face legal consequences for failing to secure their own Nexcloud instance.