If you love the bike buy it.Buy an extended warranty and you'll be ok. I have been looking into if the problem is somehow linked to eng. modification but not getting allot of answers. 
Precisely what the MOCO rep said to me 
It's not surprising that a MoCo rep who doesn't know how to fix the problem would try to deflect blame onto the customers. After all, that seems to be standard policy for both H-D and most of it's dealers. This is just one more specious claim that has absolutely no basis in fact. Plenty of stock engines have exhibited defective crankshafts, ACR failures, valve spring interference with the rocker boxes, and yes indeed, the ongoing head gasket oil leak issue. If the leak issue is due to cylinder liner movement as H-D supposedly admitted in technician training classes, why are they continuing to play around with different gaskets. If they had actually fixed the liner issue, there wouldn't be a need to keep trying new gasket designs, would there? And just in case they haven't figured it out yet, there is no gasket design that will ever seal these things if the liner is actually moving.
I think the jury is still out on the leak issue, both as to root cause and whether or not H-D will ever get it right before they abandon the engine. Just based on previous known issues that were never addressed, like premature cam chain tensioner failures, I wouldn't hang my hat on the idea that the MoCo will automatically do the right thing. That hasn't been their history, and I don't see any signs from current management that they have "seen the light". Having said all that, if someone wants to roll the dice after reviewing the facts and still buy one of these 110's, that is their prerogative. At least current buyers have the advantage of knowing about these issues prior to the purchase. The early '07 buyers weren't that lucky, and those are the folks I really feel for in this debacle.
BTW, I think the least the MoCo could do for the early adopters is to commission a special jacket in their honor. Something like "Official H-D Beta Tester" above an embroidered likeness of the 110 (a little streak of oil running down might be asking for a little too much realism). Doubtful they could be convinced to provide the jackets for free to the affected owners, but maybe they could offer a 20% discount?
Jerry