This was in the making the day they bought Indian.
Indeed the styling has been a problem since the start. The market is you buy American cruiser, you want it to look American which means retro. That said the brand has an amazing customer loyalty and satisfaction. They're built very solid, reliable, and powerful. The lack of a mid-size, entry level, limited their market exposure.
I was talking to the dealer the other day about the new Victory version of the Scout. Despite being the same bike as the Scout, same styling, a tad more powerful, and more cost competitive, they were selling ten scouts to the Victory. They say they're going to put that much more energy into the Indian line, which should be a good thing.
Knowing the market like I do, I expect there to be a glut of bikes at first, prices to decline, then down the road the collector aspect will raise values. Don't know how long down the road that will be other than to say years.