An accurate determination of these circumstances can’t really be made from an examination of the photos alone; although based on the photos and Gabe’s explanation, it does seem that there may be several paragraphs missing from the explanation.
The photographs show a great amount of dirt and sludge throughout the engine. This is significant in that this kind of contamination doesn’t occur immediately after a trigger event, but takes a fair amount of time and mileage. Some of the folks here that have straightened out a few oil burning 110’s might have some photographs of this sort of thing; although my sense is that Gabe’s photos are unique.
Engines running under the conditions pictured typically lack power; use oil; smoke; leave an oily residue in the exhaust; turn a fresh oil change black and when the crankcase pressure increases to a point, push oil through the crankcase vent into the air cleaner. The question in Gabe’s case is how long had the engine been run since the trigger event that resulted in what is seen in the photos.
Gabe’s photos show that both cylinders exhibit excessive blow-by, resulting from an undetermined trigger event. The piston skirts don’t appear unreasonably scored, indicating that the issue was not likely the result of a lack of lubrication. Evidence that the issue was the result of excessive heat rather than a mechanical failure may be found by inspecting the vat cleaned pistons as well as inspecting the exhaust guides, which become bell mouthed at the port end when subjected to extreme overheating. External evidence like the burnt clutch line seem to support a case for overheating, but things like discolored heat shields, melted plastic and rubber, etc., would be more compelling.
With regard to oiling, the orientation of the rear cylinder’s spigot, together with the flywheel’s direction of rotation, results in the rear cylinder receiving a greater percentage of the oil carried by the flywheels. When oil control becomes an issue, such as when the piston rings have been compromised, as apparent in this case, the rear cylinder will always pass more oil than the front, all other things being equal.
The tamper proof nature of H-D’s engine management controls have evolved from a couple of pop rivets securing the timer cover in 1980, to an ECM that must be “unlocked” in order to be flashed with a custom calibration. Once an operator removes the lock on the engine management controls, H-D no longer has exclusive control of these systems, and the responsibility that goes along with that control. If an issue arises after unlocking the ECM, a person might be able to determine the current installed configuration, but it is not likely that one could establish an irrefutable history of all configurations run since the ECM was unlocked; much less the conditions present throughout the tuning process.
Gabe’s engine was tuned approximately 1,000 miles prior to the eventual failure that was pictured. If the tuning effort was extensive, one would reasonably expect a series of pre-tune baseline tests to be performed in order to confirm that the engine and powertrain was mechanically sound prior to tuning. If Gabe’s engine meltdown began prior to the tuning, a leak-down test would have uncovered the problem. If a baseline series was performed and didn’t reveal any issues, then there is strong causality suggesting the engine’s calibration or the recalibration process played some role in the failure.
Regarding consistency and precedent; I believe that Chip’s issue, mentioned earlier, was the result of an exhaust valve guide dropping into the port, preventing the valve from closing. During that period there was an open “product program” which addressed an issue of mechanical failure with the cylinder heads on certain models. Chip’s machine may not have been included in the program, but the failure was a current field issue. My sense is that a warranty claim like Chip’s would be routine and wouldn’t require so much as a phone call, much less an inspection. Also, I’ll bet that the peripheral details weren’t volunteered or asked for. With Gabe, everything was on the table and on record. Dragging the boys and girls from Milwaukee up, with their pencils, note pads and cameras made that a certainty. The precedent established by H-D inspecting and covering engine damage that could be argued was caused by an unlocked, race only calibration and tuned by an independent third party, would be extreme.
My sense is that with regard to the vehicle’s powertrain flag on the VIN, you are toast; although it wouldn’t surprise me to hear that the Dealer helps you out to some extent.

as always, just my humble opinion.