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additional challenges are the inventory shortage and good contractors being extremely busy. 

Managing vacation rentals remotely sounds like a unique challenge..

@Diana Teng Buying your first rental property out of state can be a solid move, but it does come with its challenges, especially if you can’t scout the area in person.

Also, what's the nature of your business? 

One of the biggest challenges of investing in Rustbelt cities is knowing where to invest and properly understanding the cooresponding pros & cons.Here's copy & paste advice we share to help to address this challenge:-------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

My challenge is that I don't know when exactly I will be able to obtain the STR permit from the city, so I don't want to convert guests too prematurely. 

This has become challenging due to an increased interest in the historic district in Dubuque due to revitalization plans that include 18 million dollar investment into the historic downtown area. 

Challenges?

Hi @Greg StrunakScaling an Airbnb business is an exciting yet challenging endeavor, especially when it comes to managing the finances as you plan to pay yourself.