I usually attach a hose into the included tool thingmajig Toyota include with their filter and I have zero mess on the cars when doing oil changes. To remove the plastic tool, just bend 90 degrees and it pops out with the rubber gasket.
Either use a ratchet strap to pull it towards the front if it isn't lining up or use a jack stand. Where abouts in Newport Beach are you? I could maybe swing by and offer help.
Oh, I like that as well. Would you be able to throw a cargo box on top still? Like a Yakima box? Or also, would you be able to also temporarily add on the Thule Aero bars with their attachment to the rack if needed?
Hm, looking at the mounting points, can it also be mounted in those holes as well? For a more reinforcement point to the side of the frame as well as the bottom?