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

Every where you turn there are STRs going up on the market fully furnished because they couldn't pay the mortgage and bills with the rental income. 

If you still want to rent out your other bedroom you can have a tenant in the opposite side AND a roommate which would give you two income streams.

Another variable in the amount of rent that a Section 8 tenant can pay is HUD limits their rent payment based on the amount of their income. 

You have used home equity lines of credit to purchase investment rentals and want to know the best way to pay down the HELOCs.Between the two properties you bought, after expenses, you have $250 a month positive cashflow to use.What I like to do is pay down some principal every month with my positive cashflow.I use my extra active income from real estate commissions helping other investors to pay down the principal even more which just frees up that credit for me to use again.I know I can refinance the HELOC debt before it changes to principal and interest as it is just interest only payments as yours are.One difference is the cashflow, I have greater positive cashflow and could make the principal and interest payment in the future with the extra cashflow I already enjoy.I always get HELOCs on my income properties as well after purchasing them to pull out as much of my downpayment as possible.

If you continue filing taxes jointly the income you realize from your separate property will still need to be explained and redacted, regardless of the type of entity holding the real estate.

There is no current tax on rental income and capital gains.

My endgame is to end up with $300k/yr in post-mortgage income in 20 years based on investments I make now followed by continued investments over the next 10-15 years own.

Projected annual income is 20% of the purchased price.  

Hi @Andy S. 3x monthly rent for income has worked well.