Annual Rent $ 17,100 Vacancy $ 4,275 Taxes $ 2,079 Cost of Money $ 7,655 CapEx $ 1,368 Maint/Mgmt $ 2,052 Total Expense $ 17,429 Keep in mind they are also doing this at scale. 

Total which is 285k.

That just feels like a total misalignment of interests.

Looking into my first deal and stalling a little after walking through property side by side twinasking 70,000 for both sides; 2400 total square feet, 1200 each sideone side is almost completely gutted with new electrical work only.needs Hvac, sheet rock, full bath, kitchen, floors, half windows needed to be replaced and reframedother side is "livable" and "passed inspection" think feces, stains and smellsneeds new floor, full bath, kitchen, floors, half windows need to be replaced and reframed.has electrical, radiator heatmy question is I know this is a huge renovation but how do I get a ballpark?

Total renovation cost will $20,000.

Totally legal to rebate to a principal to the transaction. 

tl;dr: Total noobs looking to house hack in a Chicago north side hood.

The sell of that property was for 415k total.

The properties appraise for 75k and 100k, for a total of 175,000, and my bank just gave me a check for 50k to refi the first property. 

In this scenario, you put down 30K on 5 properties and each property cash flows before mortgage payments $800 and each property will have a payment around $700 per month (I am assuming you will end up with 5% loans and 25 year amortizations which pretty typical on investment property in my experience at the moment) leaving cash flow of a total of $500 per month, significantly less than the $800 or so you got for buying 1 for cash however you will also be paying down the mortgages at a rate of about $200 per house per month which is another $1000 per month in potential gains.