Renting short term on a sub leased property: Is it much harder? (rental arbitrage)

[John Brown]

I have a friend with a property in a very desirable location in Texas that I believe would be great for STR. It sits on about 1000 acres 30 minutes from Fredericksburg. He does not want to deal with the headache of tenants cleaning or any thing to do with STR. The property is unused most of the year.

How much harder is it to run an STR on a subleased property? Also any tips for automating this as much as possible and how to protect the property financially and property management would be appreciated.

[Katie Miller]

Are you saying you would long-term rent it from your friend and then run it as a short-term rental? 

An easier route would be to convince him to go in on the short term rental together in a partnership. You manage the headache of guests and communication, cleaning, etc. and he provides the property, but shares in the expenses and profits. It's less risky for you if it doesn't rent well and it's more profitable for him (most likely) without the headache.