But that's always the gamble.

http://www.pbs.org/wgbh/pages/frontline/retirement-gamble/Amazing what a difference the 2% fee average fund fee makes over a lifetime.

The days of associating gambling with Las Vegas and Atlantic City with the lights and the glamour are gone.

That would be the equivalent of 'speculating' or 'gambling' with your investing.

@Davido Davido Sure, you can bring the taxes current, but the adverse possession process is a gamble.

The HOAs that forego insurance are likely gambling that they will not have a claim.  

You also are gambling that a person will not send you a CDC letter.

On one of his Las Vegas trips, Ngoy took up gambling.

He gambled all of his owners rents and security deposits. 

(If a flip - you may have to do it all since an inspector will be checking it all right behind you) if keeping to rent , You can gut it and do it right now so you have little to no future maintenance issues but you’re get a lower initial return or you can do the cosmetics and gamble on the long term and take them as they come up.