I interviewed 5 CPAs, three were firms recommended by other real estate investors.

Pay the contractor for the removal and what ever else he did . 

@Marlie EvansMy firm’s managing partner works hand in hand with the IRS’ head of Depreciation if you would like to know the guidelines on the matter.

Both ways would accomplish both goals your family has set forth without losing the steady income ( The freed up cash flow and removing yourself from the day to day operations). 

The lis pendens will be removed once the house is brought up to code (demolished or rebuilt). 

@Mitchell Poloskey 1) PMI - contact your lender about requirements to remove via recognizing increase in value.

HOAs are including the roofing, snow removal and trash rest will be on me.

If the room is a mess when she leaves or she's not paid part of her rent, then remove that as you normally would from the deposit and return the rest to her. 

You could also reach out to a local, reputable, property management firm to see if they offer a la carte services for lease preparation, application processing, move in inspection, etc, if you are planning to self-manage but need some help with the more formal items.

To thrive in real estate investing, you must maintain a firm grip on your finances.