It turned out he had never managed property before, in fact he had never touch a single peace of real estate in his life, and was a renter with zero experance beyound being a sales rep for sporting goods store.In the process of trying to make the deal work, he said he would be managing the properties, but after a few weeks of owning them,  he realized he had no clue what he was doing. 

That is called gambling.

At this point, its just sport.  

In no particular order, here are the worst 5 reasons given to us for needing a commercial real estate hard money loan5 - Bank foreclosing - was unable to make payments to due to gambling addiction4 - Need cash out to pay off Mexican police to release son from prison3 - Need cash out to buy Ferrari for 23 year old Russian girlfriend2 - Bank foreclosing because charged with homicide of loan officerAnd my all time favorite1 - To get as much cash out of properties before filing for bankruptcyYou can't make this stuff up!

Not saying buying at the right time and gaining appreciation wouldn't be great, your still just gambling on an appreciating market.

If I took 50% of the money I spent on travel, live sporting events and other splurges in the last 5 years I'd have more than enough for a down payment for 2 cash flow generating houses and much closer to financial freedom.  

I think there are too many unknowns to be getting into a gambling situation with interest rates 5 years from now. 

I know many property managers that won't even manage a property with a home warranty because they are so slow and difficult to deal with.I had a friend that went to Vegas for the first time and he was really excited to try gambling.

Ring... ring.... they only had 2 boxes so I only got that, On Saturday I am going to see if the Sporting goods store has some...... ring ring.....

Be prepared for a long-term buy n hold unless the gambling or short-term rental regulations change.