I understand flippers have it the worst during a housing crash, but what about the buy and hold guys?

A slip and fall of child or hi earning person where the insurance does not over the cost of the injury or possibly a death, they could come after you personally. a car or plane crashing into the property that would be in excess of the insurance that you purchase.

Should an investor wait for the market to "crash/correct" to get those great deals?

The model I have  been working on has become far too large and crashes every time it opens.

With the housing markets booming around the country, the stock market hitting record highs, and a new political administration in the White House, are we poised for another crash of epic proportions or an era prosperity as RE investors?

My app continues to crash, everytime I message you.

He was involved in several buy and holds pre-2008, but the area had a rent price collapse in the 08 crash and rent prices got too low to cover the expenses on the properties and he lost them.

I have been investing since 2001 and went through the roller coaster of 2008 crash,  made money, lost money and came out OK. over the years, I had two evictions sued by tenant once and tenant lost in small claims court.

I'm not saying it will crash but it will slow down a bit.

I borrowed $100K to save them after the 2008 Crash and stopped payment for a year.