Considering another Short Term Rental property - help!

[Julie Halloran]

My husband and I currently own a STR property at a ski resort in New Hampshire. Last year was our first full year of owning the property and renting it out, and we think we did fairly well. We calculated our total yearly costs of the unit to be $27k (mortgage, taxes, insurance, HOA fees, electric/water/cable/internet. We made about $17k in short term rentals using AirBnB and VRBO - but because it was our own vacation place first and an investment second, we didn't rent it out on the most popular weeks of the year (Xmas, school vacation, long weekends, July 4th, leaf peeper weekends in the fall, etc). We feel like if we bought another unit that was strictly for investment, we could come closer to breaking even from a cash flow perspective.

The question is, what am I not thinking about? To me, it seems like a no brainer to invest in a property, have other people pay my mortgage and fees, and one day own the property outright without ever having to put much of my own money in it. Even losing $5k a year or so if we don't quite break even makes sense to me. So, what am I missing? What am I not considering that will come back to bite me? We have the cash for a down payment and a renovation. I guess the other option is to put that money in stocks or another type of investment vehicle.

Thanks in advance for any help!