If price are similar, as investor, I would pick the best high school - as it affects college admission. 

I offer much more content and value for a lot less cost of admission.

I see it as a lower cost of admission to the School of Hard Knocks.

At a minimum, for the next one, I think I will plan to meet with the real estate attorney in-person in his/her office instead of relying on email communications so I can get more detailed advice/dialogue, and it also sounds like we may need to find a new title company since the one we used was (at their admission) not experienced with private money lending details.

It’s not admissible under FNMA conforming guidelines.

One thing you can look for, although I haven't tried it is elementary school admissions trends.

But I just want to figure out whether or not I should apply so I can either focus my efforts on learning more about the industry, or trying to write college admission essays.

Being at the top of the class in an average school is often better for college admissions than in being in the middle of the pack of a top rated school.

The article you referenced says "In fact, the group that is most disadvantaged by our current admissions policies are working-class ...".  

By your own admission, she is asking for mostly minor cosmetic things; why not just take care of them for her and thereby create an atmosphere of good will?