My plan is to cut that in half so that I can qualify for traditional loan as I continue studying real estate and bring in private lenders.

A 2-3 hour drive to get to the property thus requiring a property manager since I work full-time, which cuts into the cash flow greatly, which is my primary goal.

That's not nearly enough margin to cover repair costs, closing costs, financing costs, realtor costs, your profit, margin of safety, etc.I'm not familiar with the property's neighborhood, but your property management budget of 8% is on the low side. 

But in front of my boys (9and10)..Right before I pull up to a property to cut the grass..

Cut your gross margin by whatever you are asking him to cut his by and reevaluate.

Hello,I am in the process of purchasing one of my first properties that after the inspection I found out a lot of garage problems.It has bad roof, rotted wood, the garage door is old, the garage opener is not working (the electricity cable is cut), the concrete is in bad shape...

That being the case no contractor in their right mind is "cutting you a good deal" on a project months away that they get paid weeks/months after they do it.

Once we inspected the property we were able to bring a safety hazard to the owners attention and negotiated a stipend for solving that issue.

You should not pay 70k for ~$650 in rent ($850 - HOA).I don't personally like anything with HOAs because I don't have control over when they are raised and each time they are cuts into your monthly cash flow and (double whammy) puts downward pressure on the asset value.The HOA doesn't cover any insurance? 

If you can get a job first that will allow you to lock down that first house hack to cut out your housing expenses that will likely be a good way to go.