I can tell you I don't know how the 09 or 10s gearing feels, yet. I will get to ride my dad's 10 Ultra in a month or so.
I can tell you about putting the Sportster 68 tooth sprocket on an 08. You do not need a new belt, although the wheel will move up in the adjustment, but you don't need a new belt.
This will add 100-200 rpm at highway speeds. I took pictures before and after when I did this at the same speed and there is almost no difference. Plus with 6th gear so tall you have room to spare.
I made the conversion for 3 reasons.
1. 1st gear was way to tall for riding in town and real slow traffic.
2. to get more performance in all gears and improve accelleration.
3. The engine builder I use recommended it and had good luck with it on other bikes.
This was one of the best moves I made for performance. I really like the results I got. I don't miss the IDS, in fact I prefer the response of a solid sprocket.
One more thing. The 09 and 10 IDS pulleys will not work on the 07-08 wheels. The wheels are entirely different and parts are not interchangable.
As for speedometer error. Mine was off to start with. The sprocket change took my speedo error from 4 mph to 5 mph error at 65 mph. I almost entirely use my garmin 850 for my speedo.
I hope this helps anyone considering the change. For me it made all the differences I was looking for. I won't change back.
Good luck.