I did the 1st oil and filter change for my wife's '08 Liberty myself last week (at about 5000 miles)..
As for the oil filter... not the best place.. the oil filter on my 98 Jeep Cherokee was MUCH easier to change... As for the factory filter.. mine must have been tightened down by an 800 lb. gorilla with an impact wrench !

Even with an oil filter wrench it took 2 of us to break the seal.
But, I have yet to have a new car that didn't put up a fight with that 1st oil filter removal.
As for Jiffy Lube or dealership.. I'm not inclined to trust either. I always do all my own oil changes on all my vehicles. Chances are, the experienced mechanics aren't going to be doing oil changes so you may be open to mistakes. My advice, always check your oil fluid level after someone else touches your car. I've seen places put in too much oil, or not enough.. either one can harm your engine.