Triedaq, my 2002 Sienna has the filter in front under an engine part. It is accessible, but the thing is horizontal which means oil all over the place. I try to change it first thing in the morning, though I realize a lot of people think you should change it hot. Over 200,000 miles so far.
I need a wrench to get it off, but put it on by hand. I rock it back and forth until I am 100% sure it is just at the contact point. Then, I put a small piece of making tape on the bottom of it. Then, I turn it exactly 3/4 turn until that tape is on the right side, 270 degrees from where it made contact. so far no leaks; no fall offs
And, I do use the nylon plug washers. I reuse them, too, inspecting them carefully. They do eventually show stress from use and that is time to change to a new washer. My son has also gone well over 200,000 miles on his Mazda with nylon washers. I tighten it by calibrated fingers, heh, heh.
As far as catching the drain oil, I first take off the filter as described with the drain pan under the car to keep my drive clean as I can. Then, I wait until the filter is all removed and the mess cleaned up. Then, I put on the new filter.
Then, I put the drain pan back under the drain plug and take out the plug. Let it drain as long as I can afford based on schedule. Put drain plug back in, wipe off any drops on motor, fill with 5 quarts, run briefly, then check for leakage.
Then, I drain the drain pan into the empty 5 quart container, and take the oil to AutoZone for disposal.
I tried when we moved to McAllen to have someone change the oil. Universally not satisfied with service any place I tried, so as much as I hate working on cars, I do it.