Air conditioning pumps are not self priming, and getting them to pull antifreeze can be tricky. When the boat is in the water the pump is usually below the waterline, so water naturally flows into it. Even then it’s often necessary to open a bleed valve to let the air out of the pump so water can start flowing. When out of the water it’s even harder to get antifreeze through the to prime the pump.
If you have two people you can try having one pour antifreeze into a long neck funnel and into the intake hose, while the other person turns on the AC and opens the bleed valve long enough to bleed the pump, and then close it while AF gets circulated.
I usually winterize by myself, so I use an aquarium pump to help push the AF through. I put the pump output onto the AC input, and pour AF down a funnel while the pump and AC run. With that the aquarium pump generates just enough pressure to keep the AF flowing.
View attachment 235321