2. You can't define anything beyond a platitude without some sort of values prioritization. Real world definitions will inherently use a value hierarchy. This is where the conflation comes in.
3. Mostly agree, which is why I said real world execution will vary depending on the value system of the population in question. The vast majority of Americans have a fairly similar idea of individual liberty as a general idea/platitude. But again, the value system hierarchy will produce different real world definitions in different scenarios. In order to go from platitude to real world application you have to invoke your value system hierarchy. Which side of any given issue you fall on depends greatly on that hierarchy.
4. See below.
5. I think we're getting caught up in semantics and don't actually disagree on this point. What is shared by the two parties is they each have the same goal: Happiness for themselves. Bob's happiness may conflict with Alice's because of how they are trying to achieve it, but again, they need to talk and sort out why this is happening so that they can get on the optimal path. I think when you say "goal" you are including the means to achieve happiness. I am not. I am simply talking about the pure emotional state. Get more conservatives on campus and we can figure out more ways of achieving happiness that are mutually compatible.