Personally I believe that our problems lie in the fact that we still seem to believe that the coach is the solution to our problems.
In the Hafey glory days, the coach WAS the solution. You could basically recruit players from anywhere, so it wasn't so hard to purchase a good playing list, and basically all you needed was a good coach with a clear game plan, backed by a strong administration, to be successful.
Richmond people still believe in that philosophy: get the right coach and the rest will fall into place. Thus we operate with a flawed hierarchy to begin with (I wish I could draw a flow diagram to demonstrate what I mean).
IMO, the successful clubs have realised long ago that the coach alone is now not the most important factor in success. Don't get me wrong, you still need a good coach, but a good coach (like Terry Wallace) will not be successful just because he is a good coach. Put Mark Thompson, or whoever you'd like to pick, into our current organisational structure, and don't change it, and he'll fail.
You can talk about 'culture', or coachs, or players till you are blue in the face, but until we genuinely treat the coaching staff as equal (or lesser in some cases) in value to talent identification, recruitment, list management, player development, fitness and medical, then we'll continue to fail.
In short, our club still resembles a suburban football club in its organisational structure — or at least it did until about 2 years ago. More changes to be made, but I reckon we are only 12-18 months into the kind of change that was needed 15 years ago.