@Tyler DavisWell....there is a lot happening in Nashville at the moment.The biggest talking point for the better half of the year has been the new Titans stadium and the East bank.

One of the biggest lessons I've learned as an STR cohost, marketer & investor-friendly Realtor is the importance of thorough market research and setting up your listing based on data.

Biggest issue is contractor realizes they have leverage over you, so timeline slips and costs escalate.

And yes, biggest risk is letting it sit for 12 months.

My biggest hesitations with keeping this property is the rental market is pretty saturated and I’ve heard of some investors having to significantly drop their rent or have prolonged vacancies.

It's one of the biggest fallacies in everyone pitching it like that.

What’s the biggest challenge you've faced in automating your short-term rental?

You asked about buying older properties and the biggest issues I have found is that roofs need to be replaced, HVAC needs servicing/replaced, and sometimes there are foundational issues (not super common). 

For me biggest challenge I always have is getting returns done and k-1s issues

The biggest challenge for being a great realtor is always generating leads and staying organized.