Are you happy with the return on that investment and do you think it will continue to appreciate (highly dependent on where you are at in the Bay Area)?

Where my primary residence is, cash flow negative, entry point for anywhere around here is too high, and I like the market out that way.

On the other hand  If you know the markets that are more favorable and attract high qualities tenants land lording can be very easy with little to no worries.  

So, either the purchase price is very high, or your expenses are high. 

Especially if you have a short high season which is also the time that you want to be there.

To @Bruce Lynn point, the rents are not high compared to house values right now - shortage of supply is driving up the prices.  

We have seen the days on market slowly come down, but it is still high compared to previous years.

I've done it four times in and around Chicago so I highly recommend it.

Both have paid rent, never late, highly qualified renters.

However, real estate values (on a national average) have never gone down over a 10-year period. https://fred.stlouisfed.org/series/MSPUSHere is what I do:I live in San Diego, a high-appreciating market with a lot going for it economically and very little cash flow.