First thing that I would do is to go to the local hardware store and purchase a longer length of drain hose, remove 'shorty' and replace with a hose that will will allow for easy fuel filter canister draining. Place the end of the drain tube into a container, lift the drain lever and unscrew the housing cap. Remove the filter from the cap and the old O ring. Clean the inside of the filter housing with a lint free cloth, place the new O ring on the cap, wipe down the cap's threads and O ring with some diesel motor oil and then snap the new filter in place on the cap. Carefully thread the cap onto the filter housing, be sure not to cross thread ( you must apply a bit of down pressure while turning the cap) and snug it down until tight. Close the drain valve and bump the starter several times to allow the canister to refill. Crank her over, should start within several seconds, if not, bump the starter again and then try cranking after you hear the lift pump stop. You might hear the mighty Cummins running rough for a few seconds after it lights up, don't worry, she'll smooth right out real quick.
While some do add fuel to the canister before replacing the filter, I prefer to let the lift pump fill the canister, thus having only filtered fuel reaching the VP44.
Scott W.