I know WikiTree is a little tough at first, but trust me - it gets better the more you work. I've been on here 15 months and I still have lots to learn.
Regarding your question about figuring out relationships:
First be sure that Mary (Cook) Wing has a WikiTree profile = so she has a WikiTree #. Then go to your home page, Frazee-227. Look in the upper right hand corner, drop down menus. Drop down under "find" and click on "relationships." This will bring you to a page where you can enter the two profiles and reveal the relationship between them. Be sure to enter it by - last name-WikiTree #.
Hope this works for you.
Oh, and a big happy welcome to WikiTree!