> am I allowed to do that only with tools that are perfectly secure?
No, actual security doesn't matter at all, but you have to think that they are reasonably secure.
> Can I send data to the cloud?
Yes, if you can expect the data to stay private
> (subcases: I own the cloud service & hardware/it's a nextcloud instance;
Yes
> I own it, but it's very poorly secured;
No
> Proton owns it and their terms of use promise to not disclose it;
Yes, if Proton is generally considered trustworthy.
> OpenAI owns it and their terms of use say they can make use of my data)
No