I used to milk my ex wife 1-2 times a day while she was lactating. Here are some proper hand milking tips that I would like to share.

Gravity helps with hand milking. When a lactating women is hand milked while on all fours, allow her breasts to hang down over the collection container. I used a tupperware bowl for this. You can kneel at her side or have her place her hands on the floor or a chair at the end of the bed while lying face down. This will also allow her udders to hang down. Hand milking worked better for us. We had a medela lactina breastpump, but it did not work as well.