A K&N oil filter is nice to put on/off with the nut on the end of the filter.
After changing the oil once with a factory HD filter I'll never use those again. The K&N with the nut on the end makes it so much easier. I usually order a couple at a time from Dennis Kirk or whoever so I've always got a spare or 2.
I recommend the simplest soloution. Become an amsoil prefered customer, you will save right there, they have choices for all types of full synthetic oils. as for the engine and primary I use amsoil 20W50 and the tranny amsoil 75/90 gear oil. You would continue to use 75/140 as you live in georgia and I am from wat the F north!