Or, say at end of term buyer-tenant can't execute on option.

Do you make them under the original owner s name or my own name ?

Yet, when I initiated a withdrawal, I was met with a complex set of terms, penalties, and withholding conditions that were never clearly explained beforehand.

I read this as someone using a short-term lens to focus on a long-term issue. 

Some focus purely on numbers, while others look at long-term value, location trends, or creative financing strategies.For those of you investing in Chicago (or similar markets), whats your mindset when evaluating off-market opportunities?

 @Greg Abel I think it's important to consider the long-term, as changing property management software is difficult.

Go after the original tenant for excessive wear and tear, also.

You might also delay refinancing until the property value or rent increases, which could secure better terms or higher returns.

If you lack the funds to flip any other way, go for it, but do understand it's not a business model for long term success. 

Eventually a nice vacation rental on the water that we can also use for short term rentals.