While it's still rough, it's not far from improving areas and revitalization efforts.While that was definitely a factor, it's still a gamble if the city improvements will translate into appreciation for me.

If you needed 1 year of appreciation to get back in the black, I’d say it’s worth the gamble.

Stock market is gambling in the short term.

Occasionally, some Brokers will send us deals that have been marketed and maybe an expired listing only to find the deal on our trash OR in the spam section of my emails. 

If you are outside those areas you are taking a bigger gamble.

There is simply no way to pose the conversation naturally, and I can tell you that people's phones, texts especially are viewed very negatively as unwanted spam that invades the personal space.

To answer your question, millionaires in So Cal (for example) don't mind gambling on continued appreciation in their own backyard (because meantime, they can afford the negative cash flow). 

If you were to try to sell that property tomorrow, you'd basically lose money.If you want to gamble for the appreciation, thats one thing.

Owning in FL is a gamble for hurricanes no matter what, so you might as well put a little money each year into insurance in case a hurricane does hit.

Leverage is fine, but gambling is not.