We are missing some critical info to really do a good look at what steps may have been missed as parts and locations are prone to change from year to year.
So what model year do you have?
Knowing which year you have will allow folks to do a check of the manual and suggest what may have been missed!
Are you doing the winterize process by following the manual? There seems to be some things missed if you are adding antifreeze and there is still water in the tank??
Can you maybe point out which step you got to before things failed?
If the pump is working but no vacuum is found at the suction hose, the most likely thing may be one of the drain valves is left open. The main point if that it is much easier for the pump to move air from some open drain than to move liquid from the jug!
Did you get the filter back on the pump good after draining it? That can be an easy spot to lose suction!
A careful run back through the process and following the manual may be the best way to look for the problem.
OR if the hose is handy, a quick way to spot an open drain is to connect water and find where the water comes out!
The winter process is tricky and may need careful following the manual as we often don't do it but once/twice a year?
I feel for you as I have trouble finding my coat after it being in the closet too long!
Winter does have a way of teaching us to pay more attention to the small stuff!