I am also involved in management at one of the largest STR property management firms in Cashiers.

There are two different servicers involved. 

And there is also a hope component involved.

.: Two things to consider: factoring in risk and opportunity cost. 

Quote from @Scott Bloom: You can get a commercial grade policy from major carriers where they lump the risk across multiple properties into one policy, reducing your premiums.  

Perhaps the most consequential transaction involving creative financing solutions was a recent closing for a 20+ unit apartment complex in downtown Eugene. 

That means creating a clear budget, forecasting cash flow, and maintaining a detailed financial model that tracks both the current and future performance of your portfolio.Tax Optimization & Risk ManagementBeyond financial clarity, strategic tax planning and risk management are essential to safeguard and grow your real estate investments.

I dont see how the risk would be reduced on second mortgage unless you are planning to hold the property in some type of llc.

Everything comes with a risk but I want to hear everyone's opinions for both states in the long run, thanks in advance It really depends on your style and goals and type of investing.I invest in multiple states and there can be some substantial differences.First decide if you want to do Flips, Long Term Rentals, Short Term Rentals, Shared Housing, Multi Family, Land, Tax Deeds, REITs, Syndication, Commercial and then decide. 

Just because it has worked doesn't mean there aren't downsides and risks. 2.