(My opinions only, of course.) The OEM filter setup is sufficient as long as nothing out of the ordinary happens, but it is somewhat limited in size. People have gotten a bad load of diesel (sadly, likely with some mud) and clogged up the stock filter. If you are traveling, at least carry a spare filter and a filter wrench, and know how to change it. And, I like the Racor coalescing filter because it reportedly does the best job of water separation.
To improve your chances of getting through such an event, I like the idea of a large filter (e.g., CAT 1R-0749 or Donaldson P553207, there are many others). I added a Nicktane auxiliary filter head down near the fuel tank over 12 years ago and ran the CAT filter. The CAT filter doesn't do water separation (or doesn't do it well), so years ago I switched to the Donaldson along with the optional glass bowl that screws onto the bottom. That way, if a problem occurs, I just at least look at the bowl for water and mud.
Our trucks are old. They suck fuel from the tank, through the OEM filter (and maybe an aux filter), and have several sections of soft lines. Eventually, those soft lines will leak (air in, probably not fuel out). For more confidence, a lift pump puts a little pressure in the lines so a developing leak should (1) smell, and (2) show where it is by the wet spot. I installed a Kennedy Diesel single pump a few years ago.
I guess there's not really such a thing as "worry free", but it sure provides a lot more confidence.
2004.5 Silverado 3500 SRW 4x4, D/A (LLY), Ext. Cab, Long Bed
engineer837 aux rad, TxC CAI, LBZ MP, Scangauge II, Nicktane aux filter head, KD lift pump, 2008 PS pump, 2011 hydroboost, Frederico Swaybars, Rancho 9000XL, Torklift StableLoads, BFG AT/KO2, Lance 835 Camper often in the bed.