I recently read the entire website without having any background in IT, with little knowledge of computers. I skipped things which involved tools/devices not relevant to me, had to Duckduckgo a lot of other things, and was still left with quite a lot of questions. So I agree with the general sentiment that the website could be improved, and that the process of improving one’s privacy is overwhelming.
But I believe much of this is down to the nature of the subject itself. It is indeed a rabbit hole, and it seems there is too much debate within the community of privacy tech-geeks to allow for the type of simplifying which you are calling for. And therefore if the contributors to this site wish to recommend something, they need to explicate why (with reference to relevant technology). For people who just want to fulfill their human rights with confidence, it is a learning curve yes.
For something more beginner-friendly, I think the TechLore Youtube channel is great, there is a “go incognito” comprehensive guide which I think would be much easier to understand than this website (but this website has the benefit of being more rigorous and update-able, I believe).
Final thought: I do not think it is necessarily overwhelming to go from no digital privacy to more private than the 99% of people. Just swap Google for Tor/Brave, Gmail for Proton, buy a VPN, Signal whenever possible and quit social media. Don’t overthink it like us. If you want to understand the weaknesses of whatever approach you choose, to be more comprehensive, and to maximize privacy without it becoming unfeasible, then yes it is overwhelming. This is because we live an ecosystem which is unfriendly to privacy to such an extent that full privacy is near impossible if you shop online or use the internet for work.