From my experience, Aircover has been covering loss of income if there were bookings for those days. 

Economic growth means higher household incomes, better employment rates, and stronger consumer confidence, all of which directly fuel demand for real estate.

@Victor Yang To use the rental losses to offset any active income (W2), you'd have meet Real Estate Professional status (which would be difficult to do with a W2 job because you'd have to work more on real estate than any other job to qualify) OR have an AGI of $150K or less.

Investing this amount in passive deals might not provide immediate income, and you could end up waiting years to see returns (similar case in most investments.) 

I knew there were some HML lenders that did OO, but OP credit score “isn’t great” (which likely means it’s poor) and “technically don’t make much money” (which likely means he has little income).i think it is long shot any HML that does OO will take on this risk for what they can legally charge for OO loan.  

Tons of returns set this system off: errors, no income lots of expenses, disproportionate expenses, etc.When all that is done, IRS has a budget for how many returns they will put in the audit queue.

My concern with declining values, increased inventory and a weaker economy would lower rental income and could potentially put me into a negative cash flow situation.

If I commit to this path, my goal is to generate a net income of $300,000 per year by December 2030.

Could you go reinvest it in another property to build even more income?

Britt,My firm has evaluated some smaller properties (under $500k) in the past for cost segregation, and it generally does not cost justify moving forward, since the benefits are small, and typically the tax liability on the income is minimal if any.