@Jordan Meltzer unless you find a screaming deal - a Class A property won't cashflow for 3-5 years.Class B: 1-3 years.Class C: most investors don't properly understand the risks, so should stay away from them.So, you may need to deal with negative cashflow, but plan on appreciation increasing your wealth.

I plan on using that equity to get myself into real estate investing.

So this involves hiring an architect draw up plans ($1,000 - 3,000 if I had to guess).  

The cash on cash return is only meaningful when you evaluate it based on your long term plans.

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

A fresh coat of paint can do wonders along with cleaning the carpet or using something like rejuvenate on laminate floors.

It depends how long you plan on living.

I currently have my investment portfolio all in North Jersey and planning on purchasing a number of units in Syracuse.

My contractor has gotten impatient waiting for him and has started taking matters into his own hands (he did the jack hammering of the floors which my plumber said had "complications" and would "take forever to get through"). 

ESP if you are planning to lowball, an agent might be more reasonable to discuss with (seller might get emotional and offended with your offer).