Oil extraction pumps - pro's and con's

Hello everyone. I have a few mowers, pressure washers, etc and changing oil can get pretty messy. I have a riding mower with a "quick connect" type valve I can attach a tube to, but it seems like it might be leaking. The other equipment has regular drain plugs, and some of them are in challenging spots. Any way, I was thinking of perhaps getting a small oil extraction pump to use on all of the engines, but thought I'd see what opinions some of you might have about using a pump vs draining from the plug.

Thanks in advance for your advice.

I have been using a vacuum pump for the last 25 years and it does work feel, it you make sure that your oil is hot. Only use it for equipment that has no easy drain plug. Good ones are not cheap, make sure you are going to get enough use to justify.

Got two of them use em every day.
As per above buy a good one, expect to pay up to $ 150 for the bigger ones.
Another case where size is important.
The 6.5 liter one will suck most ride ons out with a single charge.
The 2.5 liter one takes a dozen pump up for a ride on and even worse at least 3 or 4 for a push mower.

The vacuum pump types work very well the syringe on steroids are a waste of money as the pump seal gums up and turns to jelly if exposed to fuel including fuel contaminated oil.
I also play with vintage & classic motorcycles and have sold about 30 of them to motorcycle owners.

Hot oil is very important as cold it will take forever to drain the oil.
I usually slip a house brick under the front left wheel to help the oil accumulate under the dip stick hole.
When the pump starts to suck air, go away for 10 minutes then have another go to et all the oil that was up on the sides and has drained to the sump.
Good for sucking up fluid spills on the floor as well.

Keep in mind that some engines will have a lip at the bottom of the dip stick tube that will make it impossible to get to the bottom of the sump with the suction tube. Kohler is a big culprit.

I Use a Tecumseh oil extraction system that I purchased years ago, and have had good luck with it, but it something breaks I may be looking for other alternatives myself.