Well, I'd suggest getting the latest version of the game to make sure the Achievements work as intended, as you're playing on an old version; if you bought it on here, you should be able to redownload it and the new version will work with your old saves.
Once you've got that, then for the Hard #1 achievement (which now reads "Show Clean your benevolent Ideals after beating Path #1"), it's asking you to have a decent amount of points in "benevolent ideals" (Kindness, Pacifism) and low values in "non-benevolent ideals" (Hatred, Violence).
You have to have those once you've beaten Path #1, then talk to him. If you leave the Hub after beating Path #1, you won't be able to get this.
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For Hard #3, you should investigate the NPCs/areas with "!" above them on Path 4, specifically a certain bush. (This achievement was also made easier in the latest version; in older versions, you'd need more requirements than this.)
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Let me know if you've got any other questions!