You're gambling that the market will act in some future way banking on the 'the past indicates the future' principle.

Fix the foundation, button up the outside and let it go to tax sale in 2 years and gamble on the overage.  

Because Denver market is so insane right now, my boyfriend and I have decided that we're going to gamble/speculate.  

The city will be negatively affected if they do not diversify their product offering which is reflected in the reduction in gambling revenues and the increased emphasis by major casinos on entertainment (nightclubs and bars) as well as restaurants/shopping.Sukhbir

I have about 20k in the bank and am willing to gamble it on a big return.  

The sexy areas are a gamble on appreciation, I'd look for cash flow.I'm in Houston and can't touch anything within a 5 mile radius of my house where rent numbers work.

I have always been pretty frugal and think some things are a waste (gambling or designer clothes) but some things are worth the spending (travel)  I was actually in Vegas this past weekend with some friends who were gamblers.  

Well, that's not investing my friend, that's gambling, and ANDY IS THE HOUSE. 

I would sell now and take the loss as opposed to gambling and risking a greater loss in the future.

There is always an opportunity cost with waiting or trying to gamble.