Nice summary Dave,
Taking your advice, a good three to invest in would be...
28mm f/2.0, 50mm f/2.0 Macro, 85mm f/2.0
The only "issue" with this set is the Macro requires a 55mm filter. You could simplify matters to stay with lenses that use 49mm filters.
You hinted at the "problem" having lenses in the 35mm/40mm/50mm range... you wind up with lenses you don't use very often because they compete with each other.
I pick up the 40mm f/2.0 often and really enjoy it. I don't see why a 50mm f/1.8 wouldn't do just as well in its place.
I think a good value set would be the 28mm f/2.8, 50mm f/1.8, 85mm f/2.0