I guess draining the oil first allows the anti-drainback valve to open for the retained oil to go to the pan. Otherwise there can be a fair amount of spillage when removing the cover first. So they say.
Seems like the bypass valve is a bit delicate, again so they say, so snapping the filter in the cover and removing it from the cover has to be done with care. I suspect more careless than careful at the shops, especially when it's a rush job to get the next customer in the bay. That oil filter housing is a "piece of work" for sure and needs to be respected for its delicacy.
What I do is snap the oil filter into the base, instead of the cover. The cover goes on and comes off without the filter attached using that method and the FRAM XG11665 filter. That requires less space to do the filter replacement and no worries about the bypass valve being damaged.
Filters aren't all the same length. The body at 5" +/- 1/16", overall length 6-1/4" +/- 1/16", or something like that. Hence there can be some twisting when the top and bottom surfaces of the body are clamped to the housing by using the cover tightened to the specified torque of 18 ft. lbs.
The FRAM XG 11665 has a rotating center core inside the body, others may have the core integral with the body which means the core will twist as well. The core within the FRAM is slightly shorter than the body, presumedly to really avoid any twisting of the core.
Interesting stuff about the filters here:
Every filter, from the Mopar, to the Fram Ultra, and now to the M1, likes to think it is Chubby Checker in this engine. They all do the twist. I pulled my first Mobil 1 filter after an 8,000 mile run, and it was twisted like the others, but on one side, it was a bit worse. Close examination...
www.jlwranglerforums.com
The Pentastar's oil/filter change ain't rocket science, or open heart surgery, but it has a delicacy about it that needs to be respected.