I don't have the luxury of unlimited time and projects need to be finished within a reasonable timespan
I do pull the filter and drain plug, and resume another project, or take a lunch. So, both are off for the time frame available, and I simply use 2 drain buckets.
My vehicles do drain for 30 minutes to an hour or so, or until I get back to it. I usually get a pretty good refill amount in that time frame, more than all the clowns complaining about dipstick levels, oil capacities, and their foolishness. Take a lunch, water the garden, walk the dogs, clean the gutters,..... I have an unlimited honeydew list which allows the vehicles to drain longer than the dealershipquicklubehacks.
Overnight, won't make a difference here since drain plug location in every vehicle I've owned is pathetic. I could drive the vehicle onto ramps the night before, and pull the plug in the morning. Its all the same to me and hot/cold oil all drains out. So, I have no need to drain overnight, don't worry about the temperature, and don't care being obsessive about it.
If the oil extractor works, I find that they'll pull oil out even more with the drain plug out, because of the previous mentioned lame drainplug locations on too many vehicles. So, that is a test for anyone to see which is more capable for oil removal. Not all engines are extractor tube friendly.
https://www.skf.com/mityvac/product...pment-and-accessories/fluid-evacuators/mv7201
https://www.harborfreight.com/23-gallon-manual-fluid-extractor-62643.html
https://www.flotool.com/lift.html
https://www.harborfreight.com/13000-lb-gvwr-capacity-portable-vehicle-ramp-set-63956.html
What I don't use is the quick EZ drainplugs that some install.... a way to drain even less oil.... no sillymoto drain plugs here.
5 minutes, 1/2 hour, or overnight is for you to decide. As soon as her car is up on ramps and I'm loosening the drain plug, she comes out and... 'needs to go shopping' 'run an errand' or 'pick/drop off someone' EVERY TIME, and its always an emergency even after stating the car will be down for an hour for some maintenance. I'll make her wait some, but don't give her enough time to flip thru the divorce lawyer section of the yellow pages.