;-)I am starting to read books, audiobooks, and this site to builda basic understanding of RE investing in 3-6 months.

Also, how does one assess whether or not one can turn a profit after paying principal/interest, insurance, and taxes each month?

I price higher in other months so the lower occupancy doesn't hurt.Would love success stories on how to really attract.  

I am from the Chicago area and looking to purchase my first property in the next 3-6 months. 

A successful rental property should offer positive cash flow, meaning your rental income should exceed your monthly expenses (mortgage, taxes, insurance, maintenance, etc.).To find the right tenants, ensure the property is priced competitively within the local rental market.

The typical term of this loan is 12 months and rates range from 10%-12%.

If you have extra cash at the end of the month, then do double up payments on the mortgages so the principle is reduced and this will increase your heloc room.

I assumed a total loan of around $90k with a monthly payment of just under $1,600 using a random SF property in Indy with a similar asking price.

I'm currently grossing around $2,900 in rent per month.

There is a press release from them in nearly 18 months ago talking about how they had $1bn in agreements... https://fox5sandiego.com/business/press-releases/ein-presswi...In my 17 years in real estate, I have never heard of any group that had that much money committed without taking even the first step of closing on the land.