Tie some strings to a 3 arm oil wrench, because you know you are going to drop it. Turn the wheel all the way to the left, pop out that mud guard, use a combination of extensions... reach under there with the oil wrench, then insert the extension while holding the oil wrench on the filter. You can access the drain plug without pulling the skids. So unless you really really love pulling the skid plates... Try this out. By "oil wrench" I am referring to this design, but I have not used this one in particular:
Amazon.com: Innovant Adjustable 3 Jaw Oil Filter Wrench Tool Best for Removing Motorcycles Cars Trucks & Heavy Duty Oil Filters Fits Diameters 2 1/8-4 1/2 Inches Fits ⅜ and 1/2 inch Drive: Home Improvement