This indicates that the problem is difficult to solve at scale and customized per person. Maybe the issue is with our expectations - I find other people are pretty bad at recommending things for me as well.
Maybe. Recommendation systems definitely seem to get worse as they scale. Amazon's was incredible circa 2000. Pandora seems to be getting worse and more repetitive. Netflix kept getting better and better until they ended their contest and since then they seem to have only become worse.