If I have to go to the trouble of removing the pan or cover once, I will either tap in a drain or replace the part with one that has a drain. I even use easy open plugs on my off-road toys instead of repeatedly removing the drain plug since I change fluids often in them.
Knowing you will be doing this often, spending a little to make maintenance easier makes sense whether doing this on your own vehicles or for a fleet.
On the flip side of this, removing the cover allows you to do a visual inspection you cannot do with a drain plug. Maybe there is a reason for removing the cover?