I had an 06 with the 5.9 and now a 14 with the 6.7 and went through the same hell you did the first time. Once I got the factory gorilla tightened oil filter off the first time I haven't had too much of a problem. I do only fill my new oil filter about 3/4 full since you have to tilt it a little to get it on but I also only hand tighten it. A little smear of oil on the O'ring and all has been good for 99,000 miles. I love the new truck, but I do think that was silly blocking off the ability to get at the filter from the bottom. I have the Fumoto valve on mine so by the time I hit the switch to drain the oil, then get the oil filter off and the new one on I am ready to cut the valve off and refill it. After doing it a few times it isn't too much, if any longer than the old truck..
Now emission garbage on the new truck, I could have easily lived without that mess.