Can anyone provide insight on the average cost of insurance for Airbnbs with pools in the Boston area?

Yeap i have helped my OOS/International partners self manage. i can give you insights as the person on the ground

Thanks for the insight! 

AirDNA's rentalizer tool can provide a detailed cash flow analysis.Investment Potential: Look at historical data and future projections to assess the long-term profitability of your investment.Using these tools and insights from AirDNA can help you make an informed decision about your short-term rental investment. 

You can - 1) establish a trust for asset protection, 2) utilize the Homestead Exemption for property protection, 3) consider tenancy by the entirety for marital property (this might just be applicable to California, my home state)4) make sure you have adequate liability insurance for additional protection, 5) think about forming a business entity to shield assets, 6) and have proper estate planning for asset distribution.Seek tax and legal advice from experts in your state.

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Feel free to reach out if you have any questions or would like insight to the up and coming neighborhoods

Should I be prioritizing finding a local expert, or are there tools and strategies I can use to handle this process myself?

He has helped quite a few of my clients with their STR needs and is an expert at what he does. 

It's a mastermind, so not only classes but a community of fellow entrepreneurs with similar goals, industry experts, and accountability to get it done!