But in general, your biggest risks are not necessarily what's the maximum rent you can get, but can you find a reliable tenant that will always pay and pay on-time.

Biggest lesson I learned in this experience is to tell EVERYONE what you are doing/trying to do.

You’re trying to ruin the biggest benefit of the life in flip. 

Quote from @Agatha Simmons: Uffda.One of the biggest mistakes landlords make is failing to stand up to a problematic tenant.

NYC laws around rentals—especially short- to mid-term—can be tricky, so you’ll want to avoid any compliance headaches.The biggest challenge with this plan is finding a rent-stabilized apartment that makes financial sense and actually gives you breathing room.

I do airbnb in all my rental arbitrage, they are the biggest player in the STR market.   

@Tamika Davis One of the biggest advantages of most software on the market is to complete these tasks you mention (maintenance, leases, rent collection, etc). 

My biggest sticking point is they have severe weather; floods, hail, tornadoes, etc.

Investors Love ItOne of the biggest challenges in real estate is raising capital.

One of the biggest complaints was the lack of places to stay and the expense for such.