This is all quite an education for me, as I did not get my first HD until 2 years ago and though I am quite interested now, I did't follow the MOCO back then.
I don't mean to be rude, but always viewed a HD as a type of blue collar, American made, luxury. Not an investement to make money, but an investment in your happiness. A goal to say that you have "made it" to a certain level.....kind of like a "bucket list" if you will.
Given all of the dealerships I have visited in my travels and the economic environment, I don't see how they will stay afloat. I think many will close. The one confounding event may be fuel prices and the intrinsic fuel economy of the motorcycle. Given that the deveoping countries oil consumption actually ROSE during the last 2 years, while the US consumption dropped slightly (6M barrels/day) due to the depression/recession, when the US starts to come back on-line, prices will soar north of $100/barrel easily. Even now we are out stripping supply. Again, I would think that many of these boutique dealerships will close, but with fuel at +$5 a gallon, perhaps the the motorcycle market and HD will have niche that it can hang on to, similar to what I have observed in Europe. (many more bikes than the US). Perhaps then, an HD will be sort of an investment in your ability to cope with rising fuel costs.
I wonder if you could build a diesel HD....that may be an investment...:s