@Matt Wanyes but... is that actually your biggest concern? 

The Short-Term Rental GoldmineLet’s get straight to one of the biggest reasons investors love Palm Springs: Airbnb and VRBO-friendly regulations (in many areas).Palm Springs is one of the most established short-term rental markets in the country, with visitors flocking here for year-round sunshine, festivals like Coachella and Stagecoach, and the mid-century modern lifestyle.Palm Springs has STR-friendly laws (but with permit caps).

Securing financing is often one of the biggest challenges new real estate investors face.

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.

@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). 

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

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