A quick update:
Temperatures have warmed up (highs in the +30F range) and the miles per gallon have increased which makes me happy. I also bought a Kiwi3 OBD2 adapter and with the Torque app on my phone I can now see DPF Status. I haven't observed a regen yet, it's only been on there a day.
My dad didn't like that Ram only offered 3.42 gears in the SRW applications, so this time he went Ford. I can see why he didn't like them; his top speeds empty would barely get him into 6th. I go a little faster and find them very well suited to an empty truck.
Can you describe or post a screen shot of what your app shows for DPF status?