I tried to use the BP calculator but even then I’m having a hard time knowing what the property is actually worth, or what it will  cost to put the work that needs to be done in it before renters move in.

Calculate total monthly cost of ownership.

I have learned to calculate ARV, and reno costs roughly, although the latter I feel a bit uneasy about.

This is what I am finding in my calculations I have done as well, it seems a big challenge to get all of the money out. 

After thinking on it a bit more, I am going to look into the feasibility of a rent by room strategy to increase the cash flow and speak with some lenders to learn more details about what I'd need to provide to be able to consider these rents in my DTI calculation when I am qualifying for the next mortgage.

Great Advice, Thank you very Much, I even found a calculator to help analyze house hacking. 

Think BP calculator times 1000+ everyday. 

@Ethan Swat have you done the math to calculate the increased booking volume or higher booking rate is required to break-even on the investment?

. $800 per 2 bed /1 bath unit. quick mortgage calculator puts zero% down monthly payment at $3500, plus then offset with $2400 puts you on the hook for $1100. 

In my calculations for the Cleveland area I have 5 percent for vacancy 5 percent for repairs 10 percent for CapEx and 10 percent for PM.