Yeah, that thing looks like a booger to get out and I can only imagine the mess the oil makes. Probably gets all over the header and the pan.
What I've been doing to minimize the filter mess is loosening the filter with a filter wrench, but not unscrewing it. Just loose enough that I can do the rest by hand. Then I use a screwdriver to punch a hole in the bottom of the filter so it can drain. After a few minutes I'll unscrew it enough so the gasket loses contact with the housing to break the vacuum so it will drain faster. If you position the pan right, it will catch the oil from the pan and the filter.
It's still not spotless, but not having to handle a filter full of dirty oil (remember, I'm usually doing this on a diesel) tends to keep things cleaner. Some folks even slip a plastic bag over the filter for the final remove. I'm neat, but not that neat.
Filters with really good anti-drainback valves may not do this as well, but you should be able to get a significant amount of oil out of them.