Also, at a lower price point OR by offering more than comparable rentals that good tenant stays longer causing you less expenses for turnover/vacancy.

@Ray WhiteI recommend finding an accountant who specializes in real estate taxation and tax planning for high earners.

That sounds like a well-considered plan, and visiting in person is a great first step.

I am planning to start a direct booking site for my short-term rentals.

If they do inquire we just say we have plans for an extensive reno or the owner is requesting the unit emptied.

I would shop this out with a broker that could save you some money in the long term depending on how you are planning on keeping the property.

When is comes to mortgage debt this is pretty straightforward:"When a borrower is obligated on a mortgage debt - but is not the party who is actually repaying the debt - the lender may exclude the full monthly housing expense (PITIA) from the borrower’s recurring monthly obligations ifthe party making the payments is obligated on the mortgage debt,"  https://selling-guide.fanniema...As I understand it, when you sub-to that does NOT obligate you on the debt nor extinguish the obligation of the seller on that debt.

Without that statement it is kind of impossible to to report the rental income and expenses on your tax return. 

You don’t want to waste your time with these folks or plan 1:1 people thinking they’re “the one.”

And then proceedes to give me a list of really expensive repairs to get done asap. i have repeatedly told her she needs to contact me whenever anything breaks or is in need of repairs, which is stated in lease.