It's sometimes a little tougher to get one on an investment property vs. a primary residence but If you can get it I would strongly recommend looking into it. 

As for the property structure, using an LLC offers liability protection, while a land trust provides privacy.

Managing 20 STRs is insane, and it’s motivating to hear that the market has strong potential.I’ll definitely take your advice and start browsing Airbnb in my target zip codes to see what’s trending.

Gotta work on that reading comprehension, Drew.The second and third sentences of my post are literally:"I lived in Detroit for 5 years before moving out of state, and during that time, I built a strong network of contractors, handymen, and other boots-on-the-ground contacts.

As a realtor in the Boston area for the last ten years, and successful AirBnB owner up in NH, I’m ready to shift my focus to building a strong cash flowing portfolio.  

overbuilt. just google Austin and over delivered or overbuilt and you'll find your answer. strong market, expensive land, expensive to build. 

I can tell from your questions that you are in a bit over your head and before you make an incorrect decision you should STRONGLY consider a consultation with someone.

Estimated costs range from $500–$1,000 annually, depending on the complexity of their LLC and rental activity.For Partner 2 ($148K joint income, W-2, 1099 income, 1 rental, 2 kids), a CPA is strongly recommended.

The economy is strong here.

Focus on locations with strong population growth, growing or stable job markets, low operating costs, and no rent control restrictions.