Now that I found out that the grey engine covers are a bitch to clean, I am looking for ways to avoid oil dripping all over the engine case when popping off the filter.
So, what do you use?
Cut milk jug?
Any other clever way?

 

I spray the area down with simple green full strength before starting, which keeps the oil from sticking.
I usually punch a hole in the filter with a phillips screwdriver and a hammer, drains most of the oil out, and makes the filter a lot easier to remove.

 

I use the H-D 3/8" drive filter "wrench" deal and don't worry about the oil at all as it really only gets on the small rounded section (lower motor mount?) directly underneath. After I get the new filter on I'll spray it all down with some electrical contact cleaner and it cleans right up like it never happened. Not sure why so many have "issues" with the grey cases staining.

 

I cut most of one side out of a 2-liter bottle and slide it right up under the filter housing. Works great. Not a drop on the bike yet.

 

harley sells an orange plastic tool made to slip under the filter and it has a drain hose....it works excellent

 

here it is....

 

i just open the box the filter comes in completely and it slides in underneath the filter and runs all the way out to a bucket.

 

 

Sweet!
My orange juice jug looks just like that...

 

Just lay the bike down on its left side
Remove the oil filter
Put on a new oil filter,
Stand the bike back up