I just picked up my new '08 SERK Annie a week ago yesterday. After reading the threads here and elswhere I decided to at least get an extended 3 years (ESP); total 5 years unlimited miles. At the same time I decided to get the road hazard tire and wheel coverage for the same period. With these coverages you pick up rental reimbursement if you break down and no Harley shop is available as well as up to $150 for a night of motel if needed. I think that roadservice/trailering your bike is covered up to $200.
I'm going out on a limb here and I'm going to use a word that many cringe when they hear it, I trust my dealship (Doc's HD Kirkwood MO 314-965-0166) to take great care of my new baby and felt I got a fair deal on the bike. So knowing what I did about the pricing on the extended warranty, I still paid their price, $995 for an extra 3 years and $290 for the tire and wheel road hazard. It was explained to me that a stock RK Classic is the same ESP price as the SE version. So the SE didn't cost any more than if I had purchased a stock RK Classic. I'm not sure now that the Springer is out of the stock line up what the cost is of that ESP. The P&A book shows my wheels at $1099 F and $1235 R. It doesn't take many pot holes to have that pay off.
So with the issues on the 110" motors, I feel well protected. Come to think of it, the ONLY issues I've read about other than nit picky items, has been the motors. All in all the '07 and '08 SE's have been pretty good, with the exception of the 110" motor.
I'm sorry if I'm rambling here about how happy my wife and I are with the new SERK, but this thing runs great, handles great, smooth, stable and kicks butt in the looks department. Before you knock my handles great and stable comments, I have to say that my last ride is the infamous '76 FLH, and compared to that and my memory of my last Goldwing, this SERK is the best bike I've ever owned....
Again, sorry for the ranting and raving about my new baby.
Back to the question about an extended warranty, if we can afford to pay $25k to $35k for a toy, the extra money for the for a bit more piece of mind and extended coverage is not going to be a life changing event. It may be life changing later if you blow a motor just before Christmas and you have all the expense of the Holidays and taxes due by the 1st, the $50 deductable would feel very nice. Like years ago when this saying was popular, "If you have to ask what mileage a Cadillac gets, you can't afford one..." I feel the same about our CVO's.
Maybe some tid bits of information may be helpful with my post, maybe not.
If you have the opportunity to shop the ESP, do so. But I would recommend it just for piece of mind.
Good luck.