I don't have a Cummins but did have a 2001 Dodge with a Cummins diesel. I almost never found water in the fuel separator and I put 130,000 miles on it. I have had three diesel motor homes since then and have not found water in the separators. If you are finding a lot of water in the pick up you might try a different fuel station to see if the problem goes away. Sorry I can not help with the concern or the other items you mention but suggest you go slow and enjoy the views.
Bob, Sandi & Marmaduke the Big Pug
SW OREGON 2004 Journey 39K, 330 Cat
If towing: a 2006 Mini Cooper or 1995 Wrangler