That would never happen for me, since other than gambling, I could never achieve it in a two year time frame. 

1) Buy a business that suffered during COVID but has sound non-pandemic fundamentals2) Buy in markets where cap rates still make sense (i.e. not Canada)Investing for the hope of appreciation is not an investing strategy, its gambling. 

He was doing some extremely leveraged gambles.

Why do you think investing in Austin is gambling?

Used to gamble big time in Biloxi, MS in my youth and learnt the hard way that the House always wins.Im just trying to figure out what to do with my cash and how to invest it to be able to earn $1000-$1500 a month.

Thanks to @Steve Babiak and @David Krulac and many others for great information in this forum.Since this is first time that I actually plan to bid at Sheriff's Sales, I don't want to gamble that much money and I need your advise/confirmation. 

Then again, it's a gamble.  

Check the actual Mortgage document, which will state you must owner-occupy for minimum 12 months.If you choose to gamble and rent it out sooner and you are caught, they will accelerate the mortgage - basically give you 30-90 days to cure or they start foreclosure.The other issue is trying to get another mortgage so soon.

Not sure if he underbid the job or made a bad business decision or gambled ot away.

Vacant commercial properties are a gamble for lenders.