There are plenty of great reasons for buying a $50 drain plug. I particularly like the tool-less oil change and being able to drain directly to the jug you transport it in benefits. I'm actually a little bummed that it's not sensible for me to join the bandwagon. I change the oil in my Tahoe once, maybe twice a year so it's not a priority.
However, I'd happily drop $50 on a solution for changing the oil filter with no dripping involved. My current method is crack it loose then wrap it in a couple plastic grocery bags before removing it. It's almost a 100% clean method. Really, as long as I let mine drain for, I could just pop a hole in the bottom of it and drain it before removal. Maybe I'll start doing that.
Oh,
@Galante , the thicker (6 mil?) nitrile gloves from Harbor Freight really impressed me. I used maybe 4-6 pairs for an engine removal, internal scrubbing and reinstallation. They survived lots of sharp points, scrubs, wire brushing, etc.