Speeder, I also have an Anniversary '08 SERK.
I held out on the '07s to get the '08 with all the fixes done to the motor, or at least that's what I thought would be the case. But so far at over 3,500 miles no problems.
I would not have just gone out to buy the Annie color SE bike, but it has really grown on me and I get lots of compliments on the color and luster of the flake in the paint. You will not get that kind of sparkle with a stock '09 bike, even with the Color Shop paint sets.
With either bike the cost to upgrade to a different air cleaner, exhaust and some sort of a EFI modifier is going to be the same. As was said just a bit ago, the recalls will be coming soon and hopefully that will address the bulk of our 110" motor issues. As I said before, I have NONE of those so far.
What is the number of this '08 SERK Annie? That's the number on the right side cover emblem that's going to be xxxx/1800.
After riding a stock '07 96" EG over in Hawaii last summer, I feel the SERK does everything a bit better. I enjoy the ride on the SERK and may only do the rear shock upgrade at sometime in the future, maybe Sturgis next week if some shock O.E.M. is there pushing their products.
At $2k below MSRP I'd say you can't go wrong, but getting the extended warranty would be a nice kicker to my decision on the two bikes.
I think someone a long time ago here said that in today's market the SE bikes depreciate at about the same rate as a stock HD. I didn't buy mine for an investment, but more to satifiy my need for a bit more than the average bike. The days of buying a HD and riding it a year and getting what you paid for it back is long gone. Although if HD keeps cutting their production rates, they may get back into that condition, but I don't think the stock holders would let that happen.
I know this is your decision, but knowing what I do about both bikes, the differnce is going to be $8k to $9k between the two and that can be ate up in OCD real fast and I think you'd still be hard pressed to get a bike that will perform as nicely as the '08 SERK with the 110" motor. Don't forget the ABS brakes as standard on the '08 SERK, that's about $800 there. The 96" peforms well, but will not do what the 110" motor does. There is no replacement for displacement. This 110" motor is smooth and the torque with two up to pass cars in higher gears is great. The wheels sell for about $1,200 each, you see where I'm going with this.... The SERK has 18" up front and 17" rear which gives the SERK a totally different look than the stock RKC.
Again, this is your decision, but...... Without a doubt, I would get the '08 SERK Annie and just have a blast with it.
Good luck and as they've already said, this site will take good care of you.