In the southern US, most dealers got most of their bikes to sell in 08 in the fall of 07. The MoCo has been yakking about shipping these staggered on a more as needed basis, but did not this last year. Southern dealers will get a few more bikes to sell, and it may vary dealer to dealer, but they know roughly how many they sell in an average month, and if they do not have a huge number of bikes arriving before the 09's come out, they have little reason to be motivated to sell.
Northern dealers get more new shipments generally in late winter/spring since they have no way to test ride or sell them in the dead of winter. So to balance the factory outputs southern dealers get their's early. Out west where the weather is great figure they get them more year round but not sure. Dealers have some latitude on how they mark up & sell bikes & figure there is a hold back/rebate they can bank on like the car guys have. Some sell at list, some below, others above. Depends on the model & the motivation to sell, maybe. I know of a guy who went to Daytona & spent $3 grand more for the SAME bike since they had it in stock & ready to sell vs waiting a few weeks. Incredible.
H/D will continue on adding a frilly deal here or a clever name there & a neatly bent fender maybe on some older frame with a spiffy new paint job as long as folks line up to buy them. When that slows or stops, they will either get religion and get creative or they will just fade away. H/D has a great rep as a cruiser & that is the market they are mining. Other cruisers may rate better, but they aren't Harleys & the MoCo knows that and uses it to it's full advantage. Good business - to a point.
Economy really is not all that bad except in certain sectors despite the extreme bullchit we get to hear from various yakky heads. Housing market is bad but personal income is up for quite a few years in a row. People are not buying this year - in general - like they have in the past since they are nervous or scared. Lots of economic bogeymen to skeer the beejeebers out of them. This affects sales of big ticket items - like Harleys. Just one reason the MoCo cut production numbers on bikes this year. That was a smart move. Not building extremely reliable products, long term, is a fatal flaw. H/D runs to the brink of that with some of these problems, but compared to what I read about other bike brands - they have lots of problems too.