Jacob,I highly recommend you leverage minimizing your out of pocket expense so you can buy additional properties and have a cash reserve.

I got a book recommendation from the site (Landlording on Auto Pilot by Mike Butler) and I am implementing some of his systems to decrease vacancy and increase revenues.All of this is well worth the minimal (and deductible) cost of a BP membership!

Occupancy is minimal.

15 weeks of courses Monday-Wednesday nights, from 6-8.I figured it would be better to sign up for an in-person class to minimize my chance of procrastinating or just looking up answers for tests :) 

For Phase 2, consider painting the concrete on the entry floor and step a dark gray with concrete paint.

Especially since it is a breeding ground for unethical practices.You can educate yourself to minimize risks as much as possible and BiggerPockets is a great source to get information.

My goal is to invest in RE holdings that allow at least a double digit cash on cash return but require minimal investor involvement to manage and operate.  

You've got pocket parks in the area that might be perfect for you, but you walking around after dark may make you a bit uncomfortable.Going south to Station North, you have some interesting opportunities.

I would hope to rent the 2 bedroom unit on a month to month lease and then move in to it next year and hopefully just have the tenants in the 3 bedroom pay my mortgage and have minimal expenses while saving for another property. 

I have been burned in the past by insurance companies (as Steve B eludes to) and the LLC upfront costs were minimal going through LegalZoom and then having my attorney review the paperwork to make sure it was good to go.