Sure, I'm happy to rate both bikes based on my subjective opinion and my bias for Harleys and my long ownership history of HD motorcycles going back 27 years. Taking away the add ons I made to both and going back to pure stock to compare apples to apples, I'd rate the 2008 FXSTSSE2 a 9.75 and the 2009 FXSTSSE3 a 10. They are both outstanding bikes and I have no complaints with either, only praise. I'd love to see a company in the world do it better. They both have superb performance and are artistically pleasing. Even though HD redesigned the front brake on the 09 to a 4 piston, as I said in an earlier post, I don't notice any additional braking power on the 09 vs. 08. Maybe HD was seeking redundancy and safety that the brake wouldn't fail as a reason to have 4 pistons. I understand there are technical limitations on what HD can do with the front brake on a Springer. If you want high performance brakes with ABS over the nostalgia and beautiful look of a springer, you'll need to look for a different bike--one that everyone else owns. When I ride, I'm always looking at the springs bouncing over bumps and just the look of them from all angles.
Having rode both bikes, the 08 and 09, short and long trips, the stock seat on the 09 is a nice improvement. I think because of the wider frame on the 09, the seat was designed differently but I'm not sure how. I took a measuring tape to the two seats and the stock seat on the 09 is only about 3/8 inch wider and about 1 1/2 inches shorter than the 08 from what I can tell. The 09 is much more comfortable on longer rides. However, if you have a passenger for more than a few miles, with almost zero padding, you'll want to have a spare seat. I ordered one made for the 09 Springer from HD that matches the inlay leather and design of the stock saddle so I can pop it on if I have a passenger.
I also like the 240 mm rear tire and much wider fender on the 09 versus the 200 mm on the 08. It gives it a higher performace look and feel to compliment the 110 CI engine and heavy breather that few HD bikes have. The extra chrome on the 09 swingarm and oil tank fills in the rear with a complete finished look so now with the 09, from wheel to wheel, you have show bike allure.
Now that I have rode the 09 without a tach for a few weeks, I realize I don't miss it that much, even though I have one ordered for it. Owning the 08, I can tell what rpm I am running at just by the gear/speed I am at. On the plus side of not having a tach, the front headlight shows itself nicely with the color and paint that matches the tank and fender. Take a look at my first picture above and you'll see what I mean. With no tach it also gives the handlebars a nice uninterrupted flow from grip to grip. So now I don't know if I even want to put it on when it gets here.
I personally think the paint jobs from HD on the 09 models, irrespective of color itself, is improved with a nice 3D look (you have to see it in person) with some flair and character that the 08 does not have.
If a person is honestly objective, you'd have to be hardpressed and stubborn to deny that the 09 has some nice improvements in style and appeal over the 08. Performance wise they are about equal.