I stopped fussing with it - just remove the skid plate completely every time now and its so much easier. I like to take a good look around and wipe everything anyway....its only a few more minutes to remove it completely each time
Yep, this ^^^^ is how I do it. With the skid plate(s) removed, you can do your own eyeball inspection of everything to make sure nothing "sneaks up on you" with the drivetrain. For the oil draining, I still use the original OEM plastic drain plug and also use an old quart diff/trans oil bottle cut away on one side to direct the oil so it dumps right into my drain pan with no mess or drips. My driveway is fairly level and I don't jack the truck up for access, so the oil from the filter always runs out the rear drain trough so no mess there either. About every other change, I add a tiny bit of anti-seize to the skid plate bolts to keep them lubed fairly well, so they don't wear out too quickly.
I have 45k+ miles on my 2018, so I've changed the oil/filter 9 times. I rotate the tires every 10k miles, still on the original BFG tires. I jack only one side at a time with one big jack set right about the middle of the truck on the frame rail. It will lift both tires off enough, so I only swap front-to-rear, no side switching.