Move quickly and don't be intimidated by major rehab hurdles, just hire a contractor that can manage the project and communicates well.

@Waylon Zook There's not exactly room in the front yard for an additional shed, and it would be pretty unreasonable to expect a shed the size of a 10'x20' single car garage.

I want to write him back that we can help out, but is unreasonable for us to pay for majority on that AC unit since my parents had no say in the matter.. can I say that in confidence? 

The amount of income you currently have would pose a major hurdle unless you can show a steady increase in 1099 income.

Normally that would take less than 60 days but we're in the "new normal" where justice no longer exists, particularly in a state like NJ, and you can expect to run into additional hurdles and delays.As you're evicting them, they may decide to steal all the kitchen cabinets, smash the toilets and windows, dump paint on the flooring, and other fun tricks.

All signs point to extremely solid investment, but as a newbie I know the most challenging hurdle is going to be the one I don't see coming.

I imagine your biggest hurdle will be with labor.

You will have the hurdle of not having sufficient income to purchase on your own while in college unless you are working full time. 

Funding is probably my biggest hurdle at the moment, and am leaning towards hard money for my first deal.

Is it unreasonable to have someone apply prior to ever having seen the unit in person?