GPS & some further searching convinced me to get a Mityvac. I bought the Mityvac 7201 from Amazon for ~$90, Prime shipping.
It has been 10K miles since the last mess I made, and the Jetta was due another oil change. I got the engine up to temp, backed the car into the driveway so the front of the car where the dip stick is, was pointed down hill, and went to work.
I bought the manual Mityvac, thinking this way I could potentially use it wherever, instead of needing to be near an air/power source. There's a competitor with a similar product that has both pneumatic and manual options, but it didn't have great reviews.
Shut the engine off, pull the dip stick, crack open the oil filler cap for a vent, thread the hose down the dip stick tube and start pumping. Mine came with 3 different size hoses, so you can fit them down varying sized tubes/openings. The hoses are PEX, or something very similar, so semi-rigid but still flexible enough to snake into an oil pan via the dip stick tube.
The directions claimed to need about 10 pumps to prime the pump and start getting fluid out. After about 25 pumps with no results I was concerned. After a brief inspection I discovered the expandable rubber plug in the top wasn't sealed and creating a leak. I flipped the leaver to seal the plug, and had flow in about 5 pumps.
The Mityvac holds vacuum well, so you're not constantly pumping. Pump 5 to 10 times every 30 seconds or so.
What I don't like is that there are no graduations on the reservoir, so it's hard to tell how much you've actually pumped. I'd let it suck until I heard air and the fluid in the reservoir started bubbling, then I'd wiggle the hose around pull it up and push it back in a little further in an attempt to get as much oil out as possible. I think at one point I pushed the tube in so far it kinked a little, and was causing an issue with flow, there's a little dent from a kink near the end of the tube that supports my theory. Eventually I was getting nothing but air, and eyeballing the oil level in the 8.8L reservoir appeared to have about 4L in it.
I made the biggest mess changing the cartridge filter, but it was minor compared to the last time I changed the oil.
I added 4L of new Mobil 1 ESP 5W-30, and checked the oil level on the dipstick. The oil level was within the proper level range on the stick, so I guess I got enough out.
This will be a huge time saver, especially now that I've got a little experience using it. No jack, jack stands, or ramps needed. I don't have to remove the eleventy billion screws that hold the splash shield on. I don't have to crawl around under the car and splash nasty diesel oil all over the driveway and myself. I like the VW's top mounted cartridge style oil filter even more now. With the Mityvac there is absolutely no reason to get under the car for a simple oil change. Now that I have it figured out I'll be able to change the oil in 1/4 the time or less than it used to take.
I think that I will get a sharpie and mark some graduations on the side of the reservoir but other than that, after one use I'm pleased with my purchase.
Thus concludes the infomercial for the Mityvac 7201.