"if you try chord progressions at random until you hit something that sounds good... yes, there's a better way."
This is definitely what I meant, and it's what I currently do. My grasp on music theory is shaky at best, and I'm not exactly sure where to start to fill in the gaps in my knowledge (this may be true of any self-taught skill).
One day I may finish up my website that will guide you in an engaging way through to a good grasp of the useful stuff, but at the moment it's just some practice drills and no guidance at all. :(
Dunno if you'll even see this comment.. but my short-version recommendation is to learn different types of chords, (major, minor, 7th, etc., inversions, different spacings) and chord functions, then figure out what the progressions that "sound good" are doing in those terms. That's a big step up right there, I think.
This is definitely what I meant, and it's what I currently do. My grasp on music theory is shaky at best, and I'm not exactly sure where to start to fill in the gaps in my knowledge (this may be true of any self-taught skill).