A fresh oil filter is definitely necessary, if for no other reason than you leave dirty oil in the system if you don't change the filter.
But, changing the oil filter will not take care of the sludge problem. Sludge is varnish, goo and such, that is not captured by the oil filter.
Please, if you insist on using the topsider method, do yourself and your engine a favor. Change your oil AND filter more frequently to make up for it. And regardless of your method, remove the oil while it is HOT. This way you will remove much more of the contamination from the engine, because it is churned up and suspended in the oil.
As far as no jackstands, lifts and other safety equipment go, I use four items to change oil from underneath; drain plug wrench, oil filter wrench, drain pan and paper towels. I do not raise my car when changing oil. Obviously, I have to go inside and change to my nasty clothes, so maybe that's another item.
I pour the oil from the drain pan into one gallon jugs that my oil comes in. I then take it by AutoZone where they accept it, and I assume recycle it.
With all this said, if you use the topsider, I understand, but you can buy a wrench that fits the drain plug, an oil filter wrench, if you need it for your model and a drainpan, much cheaper than you can buy a topsider. It also lets you go further between these bottom side thorough oil changes, saving you more money.
If convenience is worth the money, enjoy your topsider and change it more often.
Best of luck,
Change oil hot and change oil often,
'01 C Class, Six Speed
'84 Euro 240D, manual, 533K miles
'88 300E 5 Speed
'81 300D Daughter's Car
Over 800,000 miles in