I guess one should have expected this especially if you ever saw empty photobucket template on old forums. They don't keep your images, at least in a way you can reach.

I mean, it would be perfectly fine but the easiest way would be a simple encryption in my opinion. OP didn't sound like a journalist to me. Of course they would be better off with at least something Linux but OS really doesn't matter for a simple encryption job, unless it's an utterly spyware like Windows.

I also suggest Joplin + password setup. It will cover all your writing needs with a good categorization. You can even connect to internet and backup it on a remote location, since backup file will be encrypted. MacOS is fine, you don't need Linux.

From what I understand, Tails would be overkill.

So, at least 1 out of 2. That's a lot!

Isn't this more like ADHD thing?

I don't know if it's true but there is saying they have more lawyers than developers.

disk destroyer deluxe

It's been 4 years already? WTF?