I don't there there ever would be a case where someone should mortgage their house (literally) and play the stock market with it.

For your best chances of success in real estate you need to play the long game. 

I just thought I'd weight in and play the devil's advocate here - because there is another perspective to keep in mind on this kind of thing.As a commercial real estate banker, I've dealt several borrowers who have had past DUI issues, jail time, and other various misdemeanors (even a few felonies).

#3 is table stakes to play the game. 

This is were we, as REI, play the biggest part since we are the ones that decide where this happens (for the most part). 

If you are good with that and want to play the longer game its not going to hurt you.But if you aren't paying with cash because you don't want your money locked up in a deal the above logic doesn't seem to meet your goals.What does the ARV look like once you get the updates completed and rents raised to market value?

if you know the road and how to manage your vehicle, debt just let’s you play the game with a faster car - and it is a blast!

Play the probabilities.

Looking to play the long term appreciation game. 

The HOA will likely have a high deductible, which is where the individual policies come into play. The