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.