I used to do extractor changes when I still had a 98 Regal GS. I would get out virtually the same +/- 5 qts of oil, and I could easily reach the oil filter through the passenger-side wheel well. This made oil changes absurdly easy. On later vehicles, either threading difficulties, or unreachable filters made it to where it was not worth doing it this way. I guess it all depends upon the vehicle.
You won't know until you do it with an extractor (vacumn) down the dipstick and then double check by pulling the drain plug. So far, for me, I'm 2 for 2. Each time it was bone dry when pulling the plug. Others have reported up to a 1/2 quart - so your stuck with the drain method.
I bought mine from JerryBeach.com - they have Pella 6000 on sale right now for $36. Works great - and will come in handy on lawnmower and motorcycle oil changes which are a real pain.
Put the vehicle on ramps to maximize the amount of oil through the plug and you can get 99%. If you have to get under the car anyway to reach the filter it makes no sense to use a pump.
Put a Fumoto drain valve on it so you just attach a hose,place the end in a empty 5 qt jug and open the valve. It doesn't get much easier.
Some makes (Mercedes, VW) have designed the engine so extraction is favored... they make an awful mess when you pull the drain plug, oil hits the suspension and other components. And as Andy said, you can get as much out with an extractor.
I'm a confirmed extractor. (I almost wrote sucker!) I used to do the classic drain method, and it worked fine on any car which was high enough off the ground for me to get to the drain plug and filter.
But then, while changing oil on my late beloved MB 420SEL, the plastic drain pan -- you know the kind, a 10-qt. pan with a screw-on cap and a closing lid, so you can take the whole thing to recycling -- the pan, as I say, began to *leak*. Not a small leak, a steady nasty flow. Sure, I could have brought it back to AutoZone for a refund . . . but I would have had to empty it first! Good thing it started to leak *before* I put it in my trunk!
I finished the change, disposed of the oil (never mind how), and bought a Topsider the next day. When I'm done with a change, I seal up the big metal can and bring it to AZ for recycling. In between changes, it sits -- clean -- in its box in the closet. And it can be used to suck out other fluids, too!