I used to have a Pela 6000 oil extractor and used it all the time to do oil changes on my old diesel Volkswagens. Feed the tube down the dipstick tube, and suck the oil out of the pan. Worked great, but I found it really messy with the black diesel oil. I sold it a while back during a garage clean-up as I wasn't using it with any current vehicles.
https://pelaproducts.eu/pela-6000/
1994 F150 4x2 Flareside. 5.0 w/MAF, 4R70W, stock.
1984 F150 4X2 Flareside. Mild 302 w/ 5spd. Sold.
1980 F150 4X4 Flareside. 300i6 w/ 5spd. Sold in 2021.
1980 F100 4X2 Flareside. 351w/2bbl w/NP435. Sold in 1995