This is a pretty general and long-winded question: Having grown up around music training, I realize that many very good musicians can't tell you much about the history of temperament or recent developments in Neo-Riemannian analysis, nor does a sharpshooter necessarily know how to perform ballistic calculus. Some do, some don't. Musicians probably have a better feel than most for what makes up a good progression, though, and can see its intricacies. What's bad, though, is that all musicians seem to think that they know the theory, because it's only slight exaggeration to say that standing in front of every deeper explanation is a simple but not very revealing answer. (For instance, 'stacked thirds' is an explanation for harmonics 1,2,3,4,5,6,7,8; and one even sees such things in the work of otherwise accomplished composers, such as problematic transformations between pitch and rhythm, or crude-but-useful geometric representations of harmony.)
I have only been on this SE for a couple of days, but I seem to see the same divide happen here, and I'm afraid that the democratic approach seems to fail too often. Take here where I clearly cite a description of the progression mentioned as typical. There is no comment explaining what is wrong with this answer, and it falls to the bottom, below a reply that calls the progression a 'fantasia', and an upvoted comment 'Everything can't be explained by theory, since most music isn't written with an explicit reference to theory'. (Sincerely no offense is meant here, and I am not claiming my answer is necessarily correct; I am just taking these examples as a sort of microcosm.) How is a chord progression with G#, D#m, F and G possible?
I don't think this happens so often on other SE sites, that answers are given that just say theory is not applicable and upvotes ensue. I realize something similar happened in the study of language grammar after the dethroning of Latin-based analysis. Still, though, I don't think you'll find many serious practitioners of logic or language who would say there are no good explanations. Instead, the field has been enriched with higher-level concepts, deeper analyses, corrections, etc., to account for as much as possible. Understanding what is understandable takes nothing away from real poetics. Similar improvements have taken place in music theory. In another parallel to grammar splitting between the philosophical, the computer-based, the speech-act, etc., musical analysis has divided into many different sorts. The serialists have their atonal number sets. The popular harmonic analysis is intended for performers. (They need to be able to read on-the-fly, and so I feel it is not best-suited to a forum like SE. Still, it is the most popular, and I don't intend to change that.)
I know that many of the top-rated contributors on this site understand musical theory and the history of theory well, as I have seen. Therefore, are there general guidelines you could give a newcomer with a somewhat-rigorous, somewhat-half-baked understanding of music, who wants to fit in here, and wants to give and get the best response?
[ADDITION BASED ON COMMENTS AND FURTHER THOUGHTS]
Ignoring voting, I think the realizations that I'm groping for are these:
(1) Prematurely answering that theory does not help to provide an explanation is likely to keep an explanation from being found or provided, at least in the timely manner required by SE. Theories and practices have been developed over thousands of years all over the world. Evidencing how the disconnect seems to occur with common theories and practices may help lead to a better explanation, however, and is to be encouraged; it may save someone effort or confusion, and also may be falsified.
(2) I suppose it is the burden of the answerer to support in detail why their explanation is to be considered 'better' than the possible alternatives, in the order that the answers are provided.