Zillow is not ideal because this is a monthly furnished rental - which Zillow doesn't have a specific platform for - but that's what has worked for me up to now. 

Are their listings detailed with good-quality photos?

So, specifically I am still curious how someone would change their approach to branding/hosting from 2 STRs that are SFHs to a 10 cabin property.

Are their listings detailed with good-quality photos?

There are a lot of good meetups for real estate investors in the area that would be good to grow your network and learn from others that are and have been in your shoes as a new investor, message me and I can share on some specific monthly meetups.Also sharing some multifamily data, this is Boston proper so it has an interesting trend compared to the rest of Massachusetts.

Now, there are OTHER things that you need, so if you could give more details then that would help us answer this a little more accurately.

Yes, they are getting higher than market rent for that specific Neighborhood, but they also have a hard time finding a S8 tenant that wants to move into and stay in that Neighborhood.

Patricia,Thank you for a detailed and a very helpful response. 

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.  

Visit with people there and you'll get a more detailed look at things from people actively working in the areas.