When Does Long Term Buy & Hold Not Work?

[Neil S.]

I have gotten into real estate in the last few months and for my real estate strategy decided on buying fixed up houses that cash flow (300-500/month) and hold onto them long term.

Many people have told me that real estate investing can be risky but it appears these risks are more often associated with speculators. People who are trying to time the market and aren't holding for the long term.

For people who are buying and holding, what has to happen for an investment to fail? I imagine as long as you can find a renter and the house doesn't fall apart it's a pretty rock solid investment. If the price goes down you just continue to hold while the renter pays off your mortgage.

Maybe someone can share their experience if a buy and hold strategy failed for them and why.