Good explanation RBW, too bad we don't have Ol' Slappy to set us straight (NOT)
As a fellow die maker I agree on all your points save for the last one.
All cutting tools (chainsaw, knives, punches, etc) experience the same edge breakdown (minus the burr) as you described so well.
You may be correct re. the burr, or roll over, caused by filing the edge however there is another factor that causes a rapid breakdown of a cutting edge.
A freshly sharpened (razor like) cutting edge is extremely weak @ the edge tip. This "weak tip" rolls over & breaks off, causing the occurrence of "microscopic" fractures that lead back into the tooth or cutting edge, allowing the cutting edge to break down further (dull) @ a more rapid rate. The harder the cutting edge, the more pronounced & deeper the cracks become.
Same goes for an ice skate blade , the razor edge first rolls over, then breaks off , causing the edge to fracture & the blade to dull rapidly.
As you know re. h.s.s. cutters , etc.............a freshly sharpened cutter will last much longer if the edge is honed (slightly dulled) thus removing the weak tip & not causing the fractures to occur sooner.
If a rolled edge is occurring from filing, this will definitely lead to a more rapid edge breakdown. As for direction of filing, an "outside in" would be the preferred direction, causing less roll over but, making the filing job more difficult due to chattering etc.
I'm not prepared to hone the edges after a filing job but, this would definitely increase time between sharpening!
Paul