I Am A Failure When It Comes To Cleaning Paint Brushes

Mainly using oil-based paints which do not clean up with just water.
Assuming house paints, artists paints are a little different because they really are oil. Exterior paints, except for traditional metal roofs, are almost always a mix of alkyds and oils and may have some resins in them - same as varnishes.
Anyway the result is they dry up faster and harder than artist paints.
Additionally, the newer low VOC versions start pulling on the brush as you work them in, in a way unlike the traditional formulations. When applying them, treat them a little more like an older latex - try to put it on so you don't have to work it so much.

Cleaning.
Spinner is helpful, but not neccessary. Spin it between your hands. Same with the comb, depending how gummed up it got - you can work it with your fingers - wear gloves.
Hang the brush in thinner for 1/2 hour or so if you have time. Just the bottom of the bristles should be in the thinner - Capillary action will move the thinner up and down (unless there is a ton of paint in the heel). Then spin it into a decent size bucket. 1 to 5 gal paint pail works. Go to cleaner thinner as needed. Keep going until it comes out clear. Then shape the bristles and put a cover on if you can. Hang it up.

Pour the used thinner into a coffee can or similar. Put that in a closed bucket. The pigments will settle to the bottom. In a few days or more, the clear can be poured off for reuse. The hard dried pigments can go in the regular trash in most places. Industrial & boat bottom paints may have their own rules.