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Thanks for the input guys. I may sound paranoid but after reading so many posts of people ruining their injectors, pumps, fuel sludge, algae, replacement costs of said parts, I figure that $300 is a small price to pay for the extra protection.
Interestingly, I followed up my conversation to Dieselcare with another phone call this morning. Our discussion digressed to catch cans and EGR block valves. Short story he said to get rid of the catch can and not to block the EGR - which really surprised me. His argument was that oil going back into the engine would keep the turbo lubricated and prevent it from blowing up, and that blocking the EGR would screw the boost in the system when the ECU decides to do a random boost test. And also that the grenade was due to oxy flow sensor, not lack of oil or temp spikes. In the end, he said stop reading all the stuff you read in the forum and besides the fuel filter, to leave the engine alone. All this is somewhat off topic but it surprises me that so many diesel mechanics laugh at the NADS..
Back on topic.. Dieselcare sent me another set of instructions for fitment to the driver side, which looks doable and is actually the preferred side (for the reasons Mudski mentioned - hot fuel). Dieselcare also said that a lift pump is not required as the OEM pump is strong enough to pull fuel through both filters without issue. I guess time will tell.