This isn't a "deal calculator" per say, but this is my personal rule of thumb that I look for. 

I know that it’s not easy to search so feel free to contact me directly if I can help.

For somone with a track record it is easy to get money for less than 50% of the profit.

Any suggestions on an easy way to incorporate this into a VRBO or AirBnB booking process?

If you have multiple properties your rates may be increased or you may be dropped because of the claim or you may not be able to get a new policy from that carrier for many years.I can't stress enough how much of a mess the insurance market is... think about it this way.Imagine 95% of the primary home mortgages in the US were unprofitable for the banks that issued the loans - how easy would it be to get a new loan?

But even a private contract does have certain issues if it runs afoul of other rules/laws, such as privacy issues surrounding credit ect.

I just highlighted it on a statement to make it easy.  

Yes, if you meet all the rules that can get complicated especially for a house hack.

.- Understand passive activity loss rules limiting deduction of losses from passive activities.Capital Gains Taxes- Be aware of tax implications when selling property, considering short-term and long-term rates.- Explore strategies like 1031 exchanges to defer capital gains taxes.Deductions and Expenses- Know eligible deductions: mortgage interest, property taxes, insurance, maintenance, and management fees.- Maintain detailed records of all real estate-related expenses.- Use cost segregation studies to expedite depreciation of your properties to offset large income gains.Entity Structure- Choose appropriate legal structure (LLC, partnership, or S corporation) with consideration for different tax implications.Tax Credits- Explore available credits, like energy-efficient or historic rehabilitation credits.Qualified Business Income (QBI) Deduction- Check eligibility for QBI deduction, providing up to a 20% deduction on qualified business income.Record Keeping- Keep accurate and organized records for tax compliance and audits.State and Local Taxes- Consider varying state and local tax implications, including property and income tax rates.Tax Planning- Engage in proactive tax planning, consulting with professionals for a comprehensive strategy.Tax Changes- Stay informed about changes in federal, state, and local tax laws affecting real estate investments.Remember to consult a real estate tax professional for personalized advice based on your specific situation.

@Kajal Aggarwal, for me that is an EASY NO!