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I'm pretty sure it is possible to get all achievements in a single playthrough (with strategic reloading). You'll need a Rapscallion and Legal background, and finish the act 1 investigation without annoying the abbot. Whether or not Andreas is welcome in the abbey depends on who he gets executed. All the achievements pop before the next save, so you can reload and play through all possible outcomes.
Continue into act 2 in bad relationship with the abbey so you can complain about your room to the innkeeper.
Also to clarify for Good Graces, you need to do all those things you listed, but it’s a lot easier to fall out of favour with the abbot as by just doing one of those actions (eg being caught at the autopsy) means you will fall out of Gernot’s favour.
Hope this helps!