You'll outgrow mentors, you'll get bad mentors, even great mentors are wrong about lots of things. don't put all your eggs in one basket, and don't shift your responsibility to learn to someone else. 

Is the assertion that because a renter is in a property for 6+ months vs. 1 week, their mentality shifts in such a dramatic fashion that it offsets all possible risk to the community?

Set aside one year's worth of living expenses in case you have losses or can't sell a property for a profit due to market shifts.

I’m willing to make a career shift as I don’t have much interest in being a contractor, some DIY skills are nice but I don’t see a great future in this industry and I’m not sure what I would excel at.

Her financial aid is limited to student loans (stafford, grad PLUS loans, etc), and work income is the occasional once or twice a week shifts. 

I currently work a third shift job that would allow of me to spend time completing a online course.

Also, opportunity to shift some utilities to tenants (trash, water, gas).Would you pull the trigger?

The first book RDPD is a good primer to shift mindset by telling a story, the best way to educate in my opinion.CFQ shifted gears and built nicely on top of that.

Philadelphia can vary heavily street by street and so can the rental prices on a garage shift as well. 

I would not portend to have a firm grasp on which neighborhood fits best into my risk profile, cash flow/appreciation potential etc as I have not lived in Milwaukee in over a decade and am sure I have much to learn about the shifts my home city has undergone.