I use the TopSider but I removed all but an inch of the Tygon tubing; I left just enough to connect the Teflon tubing directly to the metal cap. Teflon can handle higher temperatures and will not collapse so I can get the engine up to running temperature so oil is hot and very viscosity is like water. Then I stick the Teflon tube down the dipstick tube until it hits the pan. Using this method I just shy of 8.5 quarts this weekend so I am satisfied with this method. Some say that pumping the oil doesn't remove the sludge and it may not, but after replacing the rear main seal on my Jeep this summer I can tell you that draining through the plug doesn't get all of it either; the pan had a good coating that took some scrubbing to clean off.

You should always replace the o-rings when you change the filter since, they come with the filter so there is no extra charge so I don't understand why you wouldn't change them, they do break down with heat. I suspect the o-rings are Nitrile (Buna-N, NBR) since they are cheapest and are very resistant to oil, their only downside is that they are only good to 250 degrees with a shorten life. If they were Silicone (VMQ) they would last much longer but cost more.

By the way if you do change the oil through the drain plug, which I may do at 20K, you should also replace the metal crush seal; they are like $0.25 each.

Regarding the argument of paper versus fleece if you change your oil every 3K-5K I don't believe it makes any difference. I bought ten of the paper filters when I bought the car and I change my oil once a year or 4K miles which every comes first (the car is in storage about 6 months a year). Once they are gone I' probably switch to the fleece but not until then.