I think your example is convoluted. Free open source software has no contract. For a contract to be legally binding it must have consideration (exchange of goods / services / promises). This is not met.
EULAs and 'Software licences' (like MIT) are't the same thing. A EULA is a legal contract between the copyright holder and the end user, containing consideration, to which the user must agree. An open source licence such as MIT is just a declaration of permissions of use, and has no consideration.
So above it seems to me you are comparing having 'no contract' to 'a contract'.
But the DAO definitively has a contract, not a licence agreement.
Now, the DAO contract basically says 'no one can be held responsible for anything' - which in my opinion is a legal fantasy, contracts can not supersede the law. Regardless of the technological hoops in between, there are real people, with a binding contract - thus there can be tort.
I do accept when ever something new comes along and case law hasn't yet settled any technical loop holes there will always be debate, but I do think this looks pretty clean cut.