Closing IG pool

Hi all!
First day on this site! My father passed away in February of cancer. He refused to teach us how to close/open the pool, it was something he loved doing. We are wanting to help our mother this year close the pool. We are unsure how to blow out the lines. We have an IG pool. Any advice would be greatly appreciated. Where do we attached the shop vac? Should we use an air compressor?
 
My first couple years - I tried blowing out the lines - I really did. But no matter what I did, there was always water in the return lines very shortly. For me - the returns are below the freezeline - so I don't bother. When I tried blowing them, I used the shop vac right before the lines went underground.

Maybe someone closer to you has better ideas.
 
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