I used a "Topsider" rig I got from Griot's Gararge about 6 years or more ago until, when I changed the oil really hot a few times, it started to collapse. This gizmo is really a hemishperical gas can, modified to take a vacuum pump. The little tubes that come with it and suck the oil out are hard plastic and never came close to collapsing (the can did that instead).

I am a believer in the "change it hot and change it often" mantra, so I researched the available devices. I found a boating accessory,(getting to a sump drain plug on some boats is likely something you have to be bred for) that was designed to work on hot fluids, a Sureflow WaterWolf or something like that. This thing is electrically powered (from the car battery) and can hold at least 5 gallons of waste oil. It pumps the stuff back out if you want into more manageable containers to take to the recycling place (highly advised).

Anyway, I change the oil after a 20 to 30 minute ride when it is at full operating temperature now, and other than having to watch the gadget so it does not pump oil all over the driveway again when transferring the load to something I can empty at the recycling center, I find the device worth the heavy price tag ($150 plus). In my gas cars the oil is never full of junk (Mobil 1 0W-40 or , 15W-50) and in my Diesels, which also only use synthetic oils (Mobil Delvac 1 5W-40 or Mobil 1 15W-50) I do not think there is anything of significance left in the pan. I typically run the pump until it is sucking air, then let it sit and the oil drain for another half hour to an hour and try again. I keep doing this until there is no significant additional oil getting sucked up and then go to finish the job.

I have done this for years both ways, and recall the dread of changing the filter on my 1974 240D. I never liked hot Diesel oil on my arms or hands either and that car's filter location was a nightmare, especially getting it back into position without getting any dirt on the "O"-ring.
The best thing going for the devices that suck the oil out of the dipstick tube is they are more convenient, and therefore you are more likely to change the oil. Good Luck, Jim

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Own:
1986 Euro 190E 2.3-16 (291,000 miles),
1998 E300D TurboDiesel, 231,000 miles -purchased with 45,000,
1988 300E 5-speed 252,000 miles,
1983 240D 4-speed, purchased w/136,000, now with 222,000 miles.
2009 ML320CDI Bluetec, 89,000 miles

Owned:
1971 220D (250,000 miles plus, sold to father-in-law),
1975 240D (245,000 miles - died of body rot),
1991 350SD (176,560 miles, weakest Benz I have owned),
1999 C230 Sport (45,400 miles),
1982 240D (321,000 miles, put to sleep)