Im sick of being stuck on this and not getting anything done.

Maybe your Aurora houses could 1031 into an apartment building to reduce vacancy exposure and increase cashflow over time.

Therefore the demand for student housing has increased while current owners await insurance settlements for their damaged properties.

Using equity from my primary residence and then the 2nd mortgage approach will obviously increase my debt. 

First, check how often the HOA dues increase. 

Current situation I recently moved back home with my mom to increase my income and pursue my education full time ...

On the other hand, by house hacking you may achieve the same living for free scenario or let’s say that you are $100-$200 out of pocket, but you will also benefit from principal pay down (you gain equity with each mortgage payment), tax breaks, inflation (each year your rent may increase, while your mortgage payment stays the same), and appreciation (maybe).

Use your cash to invest in a different property and increase your cash flow and assets.

Tenant lease was up and I needed to renew the tenants lease with the increase.

A property can only actually increase the cash flow it puts out one of two ways...either increasing rent or decreasing expenses.