I got converted when my 190E 2.3-16 drain plug got stuck a number of times and had to be destructively removed. I bought a Topsider from Griot's Garage and have never looked back. I am not too dull about these things, so I was very careful not to leave a part like a washer out or to tighten the bolt too much. It is the only car I have had this problem on and it is the only one I have seen with a plug that has about an inch and half to two inches of thread. It also has a belly pan, but leaves some access to the drain plug.
The 1991 350SD was another story. It had a belly pan that had a number of fasteners on it, but they were not the kind that were intended to be removed every month or two for an oil change. While my preference was to pull the drain plug, I gave up the second time around and used the Topsider.
I agree with Larry in that one big benefit is you are likely to keep a frequent oil change schedule using a Topsider. With more frequent oil changes, it is more likely that any small quantity of left over, undrained oil will be benign. So, it turns out to be a matter of choice. Good luck, Jim
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
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)