You've probably heard of big Landlords losing property, but only because they were flagrantly violating Fair Housing, running a slum, or otherwise violating the law in an egregious manner.

Make sure property is “self supporting” meaning sufficient income to produce some cash flow after operating expenses and debt is paid.If one does that, they are set up for a profitable long term hold.If one invests in a prudent manner and is never in a position where they have to sell, they ultimately win.The top or bottom of a market is never known until 6 to 12 months after the fact.I’m a long term investor - my capital is patient.Here’s a question to ponder:If you could buy a property today for $1M, knowing it’s value would drop to $950,000 over the next year but would be worth $1.5M in 5 years, would you buy it today or hope to perfectly time the market and get at $950,000?

Equity split meaning on the refinance we split the newly-discovered equity in some manner (50/50, whatever we come to, etc.) and then I keep the cashflow? 

For instance, an apartment complex would provide good cashflow however, it would be quite difficult to sell in a timely manner if I needed the money.

The only way to sustain your current lifestyle is if rents rise faster than inflation.

In nearly all cases the tenant is paying in a timely manner.3.

Does anyone have a recommendation for a Chicago architect with experience in the City of Chicago, and who has the proper sustainability credentials?

You just want to make sure that it's a purchase that can sustain itself while you wait for that land value to go up and up. 

In this case it happened in a timely manner.

I believe they’ve crested and will not be able to sustain their revenue growth.