Define, (actually define) the "stability" and "energy" of a compound When we say a conformer or compound is of "higher energy" than another, are we quantifying energy in terms of the bond strength? Or are we going off of how much energy it takes to break the bond?  I don't think we can just assign energies to each compound... so what is this based off of?

One might answer that its based off of stability. Well, what is "Stability?" Is it how rigid/strong the bonds are? Is it how reactive the compound is? 

Often times i find myself reading explanations with circular language on this topic. A higher energy conformer means lower stability or A stable compound is one that has low energy. I'm finding these definitions to be crazy ambiguous, and don't thoroughly define what these are.

If someone can clearly explain this in terms that a first year undergraduate student can understand, you have earned my gratitude.
As a chemist, I would agree that textbooks are not clear about the term stability and energy. It is not your fault and undergraduate organic chemistry books make the situation worse. I cannot recall the text, it was an old book, however it clearly said that stability of a compound does not mean anything. We should always ask, stability with respect to what? Are we talking about thermodynamic stability or kinetic stability? For example H2+O2 mixture is not stable. This statement is meaningless because we are not saying stability with respect to what? This mixture should form water right away but people actually waited for 30 years and did not find much water in a mixture of H2 and O2. Thermodynamically, this mixture is not stable and it will react violently once you provide the right activation energy. When you are reading about stability, ask this question yourself.

In the same vein, the term energy should also be clarified by authors. As a crude analogy is that you can think of energy as the potential energy of the whole molecule when the authors talk about conformers. Have a overall picture of the molecule. Imagine two springs, A) one which is less stretched and the other one (B) is more stretched. You can say spring B has more (potential) energy than (A). An eclipsed conformer has higher potential energy (overall, no need to think locally) than a staggered one.