My guess is they brought in the auto guy to do exactly that. There are some clues that's going to happen in their accelerated strategy, this is exactly what car manufacturers do to make sure they hit their market mix -- the dog wags the tail.You may be onto something. Adding additional dealers that only carry the small bikes and electrics leaves the old dealers to carry the big bikes. That fixes many of the problems and can work well (I'm thinking like VW/Audi, Honda/Acura etc.). If a barge dealer wants to sell the other bikes, they can, but those that are worried about diluting their barges with adv bikes can remain with the current line. This gives HD more dealerships (although I don't think that is their problem) but more importantly puts the bikes in the hands of a sales team that loves them and isn't focused on sliding buyers into the higher profit bikes.
The other way for HD to update the dealership culture is to meter out the big bikes. Let the dealer have a big bike for every two of the new design bikes they move. That incentivizes the dealers to care about the new lines. Those that crap on them will get steamrolled as they won't have stock to work with.
HD has struggled to get their dealer base to move off the hog. The Vrod was moderately successful but did not sell well enough to survive, largely because dealers only sold them to riders who asked for them -- even then they would always try to sell a hog first. The Street line has had dismal sales so far, much of the blame has to be on dealers, they simply don't stock the bikes - the tail wags the dog.
Having smaller urban dealers also reduces dealership overhead. The existing dealer network operates from large stores that resemble car delaerships, not bike shops. By lowering overhead makes selling smaller and unique bikes profitable.