Ok, if you're going to use a Pella, then you go through the dipstick tube.
From my experience, I take the cap off the oil filter first. This lets the oil in the filter housing drain into the sump. Then I put the Pella hose down into the dipstick, pump it up and let it do its thing. While this is happening, I get the oil filter ready.
You'll probably find that when the Pella gets to the bottom of the sump and starts making that 'empty soda straw' sound you should move the tube around to get the last few drops of oil. Then put the tube into the bottom of the oil filter housing, there's about a half pint in there.
I pour the new oil into the oil filter housing (before putting the filter inside). Bigger target. You're going to need around 4.5 quarts. You should start with 4, start and run it, then top it off.