It doesn't happen slowly, it happens like when the "Flash Crash" took place.

At least when the crash happens, they won't have the money to fight people who know what they're doing.

When the the S&P crashes, so does the value of your mutual fund.

I am planning to move to Boca Raton area soon.I would like to buy a 4 bedroom , 2 car garage home with swimming pool.I am wondering how much property prices have appreciated in last 5 years.Is it worth to wait for couple of years and hope to see market crash or just buy it now?

It will be hard to repeat the same modest success I’ve had due to that last housing crash being only once in a lifetime.

I know we saw a ton of them after 2007/08 crash but how are these sellers ending up underwater in our current market? 

It took forever for the market to make it not underwater from the crash. 

Those indicators that showed the crash last time are watched today.

For example, how would an apartment building lose its value in a market crash, and be tough sell?

So make sure your numbers are good in that area.It could still become a profitable rental by not taking out ALL the equity. ie, buy some cash flow.The BRRRR method is likely less doable now since property prices have recovered from the crash discount bargain basement prices they were at for several years.