(Rhetorical question) Weigh your alternative and get involved in a way that you are most comfortable with.

An alternative viewpoint:http://www.dailyfinance.com/2014/07/19/the-worst-i...

Is it worth it to do this repair and if not what's the alternative?

It's human nature, if you look around it's not just tenants or poor people who exhibit behavior like this.

The path of least resistance considering your experience is more ideal than the alternative.

She is a woman who naturally garners respect and that's someone who I want on my team.

If you are a naturally good sales person, are honest, ethical, want to have a lot of fun doing real estate deals, are seeking an opportunity to make great money for the effort you put in and you are interested in working with real estate investors every day, this position might be for you.

If elementary school quality is a consideration, focus on Ditto, with Little Road being a solid alternative. 

The natural reaction to a rent raise is to be unhappy, however if the tenant knows they've been "getting away with it" for a while, they may not really get upset, even if they show disapproval. 

Hell, you may even be better off taking a HELOC against your current residence or something of that nature to get the extra funds.