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.

Let the compounding effect of time take over from there.

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.

If not, I would highly recommend doing so!

I've done some localized studies and the numbers of owner occupied buyers versus investor buyers in several of my current markets are 10 to1 ratio and as high as 25 to 1. 

Now I'm getting to the point where it's starting to impact my credit score due to high utilization so I'm going to refi 3 properties and pay off all the cards.