There is a massive difference between talent evaluation for the college game and for the pro game.
DeShields is a 6-1 guard/wing who is uber-athletic and can create her own shot. You cannot teach those things. You can work on shooting mechanics (which she needs) and defensive effort, but her ceiling is much higher than that of Plum.
Plum has had an amazing college career. She is, however, much closer to her ceiling than DeShields.
Mitchell is more athletic than Plum, but Plum is more efficient. Mitchell is still adjusting how to play with better talent around her (which she did not have her first year. as an example). This may be an issue in the W - playing with better players and contributing when the ball is not in her hands - when she will not be the focus of the offense (and may not even be the 1st or 2nd option on offense). Plum is not as quick, but being the focus of the opposing team's defense has turned her into a player who is much more adept at creating space, working on a quicker release, and her movement without the ball.
Brionna Jones puts up great numbers and is a force in the post. But she is undersized for a WNBA center and is able to physically overpower her opponents in college, which she will not be able to do in the WNBA.
But DeShields is - and should be the top pick - for a franchise that believes its coach can develop her on both ends of the court to reflect the conversion of her limitless tools into tangible basketball skills and consistent performances. And San Antonio has a huge need at the SF position. Diamond has also never played collegiately with a PG as good as Jefferson (or even a playmaker who was better at that skillset than Diamond), so this will help her overall game.
Chicago is set at PG - Vandersloot as the starter, Faulker as the backup. Dolson is a starter; the only question is whether she will be at the 4 or 5, as Chicago does not have a stretch four or forward with guard-like skills like Delle Donne to put there. What Chicago needs is offense; EDD was over 25 percent of Chicago's points. Plum can provide that in droves. And Cappie Pondexter, who has been the starting SG, is 34 years old; Plum could easily be the heir apparent.
In terms of both talent and fit, I believe DeShields (#1 to SA) and Plum (#2, to Chicago) are right where they are supposed to be.