We're relatively new STR owner/operator in Highlands and have been very pleasantly surprised with demand even outside the peak summer season.

Id recommend the single-family rental because you have more control and you don't need to worry about some greedy operator screwing it up 

Opening a new fund or operating company and not reporting on the old fund’s results3.

Hi, we are a small operator with 14 doors and Grasshopper told us we can't send texts anymore because we don't have a website.

OOS investing has operational inefficiencies, because you work remote.

Ask specifically what is needed to comply. 

One workaround could be keeping a separate spreadsheet to track your adjusted tax basis accurately and only using Stessa for operational insights.You could also reach out to a cpa and see if they have a specific recommendation for software to use.  

These repairs are through a contracting company owned and operated by the PM. 

I see a conflict of interest in your role as fund manager and principal in the “operating” company.

Therefore, your financial freedom hinges on new companies continuously moving into the city, creating replacement jobs.Companies have many options when selecting a location to set up operations.