I've tried the extractor, and pulling the drain plug gets more oil out, in all three of my vehicles. An extractor leaves me with a few questions. For example in this post people are concerned with getting as much oil out as possible, draining oil overnight so they can get every possible drop out. Oil can take several hours to drain from high places in the engine and get to the pan. Two beers and an extractor isn't getting that oil out. I've extracted oil, couldn't get another drop in the extractor, then I pulled the drain plug and got more oil out, leaving it out for half an hour. That might have put me to beer #3, etc, the longer I let it drip. Granted I didn't get much oil, only a couple of ounces at most but for the purpose of this thread the extractor imo falls short.
Having said that how much longer will an engine last allowing oil to drain into a collection pan overnight? My bet, not much with sane OCIs. I recall reading about people starting their engine with the drain plug out to try and get more oil out, others pouring fresh clean oil through the engine to do some extra cleaning on the way down to the pan. No comment on either of those practices. At some point the OCD has to stop.
Regarding the extractor it is a great tool, and on certain vehicles an asset for changing oil. My drain plugs are easy to access, and two of my three vehicles I have to get under to get the filter. So it sits in a box until I do a transmission service, or something else requiring it. It earns it's keep pre-draining ATF making pan drops much easier.