You would want to make sure that their rent payments actually gain you a profit and that there isn't any penalty for selling in a few years.

@Ashish Acharya I want to say it was capital gains tax if you dont keep it for a year or so.

$100k gain is my minimum to bother with an exchange. 

Then a recent one REALLY caught my attention and made a lot of sense to me.

The 3 year mark from the day you move out is important since it will be the deadline you have to decide whether you want to sell or keep this property without having to pay capital gains taxes. - Please notice that you won’t cash flow the $30k (minus repairs, vacancy, taxes, etc.) that you calculated, since you will have to pay interests for the HELOC

The incentive for investors is the deferral of capital gains taxes in stages over a period of years. 

(Question should be viewed as theoretical and does not necessarily reflect our true financial situation) I would pay close attention to make sure it is ONLY due to depreciation.

I'm sure the experts have gained experience from on the job, but how are beginner investors supposed to determine on a whim what will need fixing and how much it'll approximately cost? 

Considering you're a Pro, I was hoping to gain some info as to whether or not a property that I am about to get under contract is a concrete deal.

The business will first focus on building up its property management division of the business to gain immediate access to cash flow and profitability.