5.9 Magnum dipstick

Im using the stock serpentine belt setup also, do you know if a trimmed Magnum style dipstick will clear the windage tray?
Yep, enters the block in the same location as stock LA, just make sure you round the tip and give it a bit of a twist like it had from the factory.
The LA tube projects approx. 11" from the block, and the stick is 21+ and goes about 9" into the (center sump)pan. That 9" is what you're aiming for. The magnum tube is about 16" out of the block and the stick is 35+" long, so to get that 9" into the pan you'd have to trim about 9" off the Magnum dipstick, taper and twist the end. Measurements are approximate, confirm yours before you cut.
To make the marks, add 4 quarts of oil and insert the stick- note the level and mark the stick accordingly, scribe or lightly file new marks using your oil level as your midpoint. Note that the fifth quart of oil is added later- it will be taken up by the filter and system and should not be considered when marking your pan capacity (stock LA pass. car pan).
I have seen even stock dipsticks interfere with the factory windage tray a bit, just test fit the stick a couple times before you button up the bottom end. A "touch" of clearancing on the tray wouldn't be unheard of. If it's an aftermarket tray/screen (non Chrysler/DC) I've heard of issues- clearance as needed.