In my experience, what it boils down to; ESP has covered some modifications in the past, and between the Dealer and ESP, the claim process (whether stock or slightly modified) has been relatively painless and efficient to the Purchaser, but recently ESP will not accept any claims that do not meet the letter of the contract, and even at that, customer satisfaction with ESP seems to be on a decline. On the other hand, it comes down to actuarial data, ESPs bottom line, and Harley's recent shortcomings.
Within this thread, bigskyroadglide's Skunk was stock at failure, and;
(Post 119)
"it was nothing like upfront and painless. If that was the case, i would have gotten the engine repaired a lot differently.
it was very painful and took too long & created needless hours of missed riding over the course of 4 weeks. Then of course its a $33K bike that experienced catstrophic engine failure at 18K miles. WTF is that???"
(Post 1)
"So ESP sent a inspector out (very quickly too) and i am waiting after an overnight stay and a 600 mile rental car trip home to hear about my bike."
Other than bigsky's catastrophic failure of a premium Harley product at 18k (I had 2 failures in 22k ~ professionally adult ridden ~ properly maintained ~ I'm not very happy about the '09 with the MoCo at this point...) I feel that 4 weeks (for bigsky) is a reasonable (3 weeks, would be very impressive) turnaround for a complete rebuild including #s matching cases, I would be curious as to how satisfied bigsky is with the way his Skunk runs, after this drama, and how many miles until (if?) another claim (failure).
The '05 SEEG; (bone stock) still has ESP and it is comforting.
The '09 SERG; ESP denied the claim for the same (front intake lifter / catastrophic ) as bigsky because of a SE Stage III Kit (all HD) ~ my Dealer's reasoning was that since the 259 upgrade is "street legal" in a 103, then the 259s would have ESPs blessing ~ not so... (ESP would not accept any mods whatsoever to reinstate) I cancelled ESP...
My short take;
Read the contract (what will be / not be covered), if you can enjoy your Harley within the parameters of the contract (basically no 'mods) then IMO ESP is a worthwhile expenditure.
Don't purchase ESP until very near the end of the factory warranty period (they will hit you with overlap, if you let them).
There is approximately 50% margin for the ESP selling Dealer.
You can cancel ESP for a rebate anytime.