This is one of the longest running problems without a solution i have ever had (it caused me to seek out alternative clients in the first place)
Anyway, heres the deal: Youtube doesnt seem to remember my history on any video, heres the things i tried: check of history is in (it is)
ad these to ublock origin .video-stats.l.google.com .s.youtube.com
disable ublock origin
try a different browser ( fresh firefox and two different chromium ones)
disable tampermonkey

And today i looked at my history again, and the weirdets thing is it does remember the position and when i open the video from googles watch history, it works, i opened a video normally after that and it worked too

Anyone with any idea what is going on here would be greatly appreciated