Where 'bouts you located in Indiana. You need to check out Kerstings HD in North Judson. We got our '08 Heritage from them last September, and love it. There are more than a half dozen dealers closer to us but the Kerstings are super to deal with, and I'm convinced worth the extra miles.
Jason Kersting is the sales manager and he is a totally non-pressure guy to deal with. If your not sure what you want, he'll patiently show and explain to you the differences. When I was pretty sure I wanted to go with the Heritage, he asked me if I wanted to try it out to make sure it fit. (Wasn't a demo day) He shoved it out of the showroom door and down the road I went. Yeah, that was the clincher, but I was 99% sold on it before I rode it.
I was up there about a month ago and they had a pretty good stock of '08's, a couple '07's and several used rides. There is also a very nice motorcycle museum in a separate building that makes it worth the trip whether you buy anything or not.
Check it out, ask for Jason.
Their web site is Kerstings Cycle Center-North Judson, Indiana
I work in Indy east side, live in Crawfordsville, long commute. Plan put a lot of miles on the bike this year. After you get your bike, maybe we can hook up, got several buddies in their 50's that love to ride.
Like I said, check out Kerstings, the museum is unreal. Lot of info on their website.
The HD 6 speeds in the 06 Dyna had a problem early on with poor bearings and anyone that purchased one of these bikes had to bring it back in and let Harley replace the trans bearing at the MOCO 's expense. They finally changed bearing suppliers and ever since then , there hasn't been any problems with the units.