Usually when the property is in REALLY poor condition and can currently not produce any income OR for properties over $1M and above where financing is really hard to get.

An exhaust fan shouldn’t produce cold air.

I see what someone is capable of before allowing them to do any significant amount work and if they aren't good, steady workers, aren't trainable, don't listen to instructions (and I have someone that knows how to do whatever is being done ON SITE, or produce poor quality, I shut it down-- Thank you for your help, your credit is $xx, I'll credit your account tonight, that's it for today.

So, basically those are the numbers I'm using to evaluate if my time is being well spent, given my other options - which in my case might be things like pursuing other business directions, leisure time, or going back to the W-2 work of engineering (or trying something different).The ongoing cash flow from renting the places out can add additional value, but the way I think of that, I'm more interested in evaluating the needed ongoing time commitment to servicing those rentals to produce that income/free cash flow. 

And if the rental is not a top producer for you the additional leverage can turn it from mediocre to bad very quickly. 

I’ve given the example on i have a property that cash flow negative $400/mo while producing a $1,000/mo income.

And that's why the 1031 is such a key tax mitigating strategy.If you have several rentals then the idea that keeps the tax dollars working for you is to consolidate those rentals into passive cash producing assets and live off that cash. 

So long run there are two advantages. 1- invest the tax savings to earn income, when the tax savings are recovered by the government later you only pay what you would have paid earlier but get to keep the income produced by the use of capital.

@Conway MorganLook into being a buyer's agent on a top producing team.

If it is just a single family, then the income it produces will have less of an effect on the sale price as your primary consumer will be an owner occupant.