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^ Owned a small fleet of tow trucks and drove a diesel dually as my daily, know exactly what you mean.
Just go in to the purchase with eyes wide open. If you're comfortable with having a bigger repair budget at the ready and know that you're paying a premium for what you want, own the fact that it's a decision born out of want and not need and get what you want. If you get anything 07.5 or newer absolutely get something like an Edge monitor to keep an eye on exhaust temp, soot levels and other indicators that your emissions system is functioning properly.
6.7 Cummins are the "easiest" to do work on of modern trucks (cab doesn't have to come off for things that it does on GM and Ford), followed by the Duramax's, then the Fords. My recommendations for more modern diesels would be 2009-2012 6.7 Cummins or a 07.5 to 2010 LMM Duramax. The LML 11-16 Duramaxs are my next choice but they have DEF so that's an added complications. Personally wouldn't touch a Ford that wasn't one of the Alumiduties, they really seemed to figure it out with those trucks.
I love my 2016 ram sport 1500,l.looking to mabye upgrade to a new truck next year,probably be another ram 1500 hey Laffs where do you work at?