It would be a big gamble to buy this thing and not break even and then enter into any sort of issues with maintenance or finances.

It might have enough appreciation to offset all the money you throw at the house in payments and maintenance, taxes, etc, but if you want to gamble with your money, there's better ways to do it.I think you need to start with goals and decide if this deal lives up to your deal standards.

Have you ever gambled any game in casino when you were in Vegas?

We're not talking SF-over-the-last-10-years appreciation, but I'm interested in predictable investment returns, not gambling.

You do not want the neighbor listing on mls or other network because you have no way of knowing what someone else will pay for the place (of course, it could also work in your favor but that too is a gamble).

I can gamble and wait till I sell my flip but not sure if the timing is going to be right.  

Where you get in trouble is usually when you try to raise money for business enterprises or investment purpose.

Basically expenses incurred to operate or expand an existing enterprise could be deductible.

I think speculating on amazon would be a huge gamble at this point.

If you, based on market indicators, believe that there will be appreciation then hold on however we all know that's a gambling mans game.