I am mentally prepared to lose money as that is a risk of investment and it may all work out in the end but it has been a roller coaster of emotions!  

In more cases, they will have better risk management processes than Joe-blow seller who's owner financing.

It's those maniacs that buy homes cash via quit claim deed off of craigslist that really get screwed.Make sure your property manager is a licensed real estate brokerage.Understand you can not eliminate all risk, only mitigate it.

At the risk of sounding elementary, I'm asking what I really need to now.I've come to believe that BP is THE place for REIs and no one else is better equipped to help us than us, so here goes:1.

Or they should simply tell us how long they're able to commit to and we'll run this as a short term lease until they have more clarity on their situation or move out, but it doesn't appear the tenant wants to pay a dollar more.So, basically the question is - do we take a leap of faith and lose our peace of mind or insist on sticking to the contract and risk losing the tenant?

Oh, and willingness to take a risk.

At the risk of appearing like some weirdo, I actually recognized your name from the property records I've pulled over the past 18 months in Pittsburgh. 

If the numbers crunch in your favor and you have the means to execute on the sale, you know the saying, "No risk, no reward".

If the guy/gal already has an Airbnb business with his/her reputation staked to it and they just want to expand it (and especially if they own any of their portfolio), why are they a galactically bigger risk than a long-term tenant (who comes with risks of his/her own)?

I should also mention that if I do a rehab, I would like to start with more of a "remodel" so that I am able to start small and build up my risk tolerance.