Further, there's around 20 items on autopay, newspapers, cable, internet, phone, medical insurance, etc.

To you, one way for you to reduce your cost of putting up multiple LLCs is to deed the property to a LAND TRUST and assign someone you know & trust as the trustee (and have different trustee per property). 

Are you willing to sell at a reduced price if you can sell it quicker?

I inspect my own properties once a year, I try to take care of the things that reduce later damage like cleaning the gutters and servicing the furnaces.

Same with the hit on sales price, they don't want their buyer going down some wonky loan rabbit hole over a $1000 roof leak, that's going to reduce the sales price they can get by a LOT more than $1k.

My buyer is in need of mitigating his medical collections payment, and I remembered hearing on a BP Podcast that “just paying it off” once it hits collections is the worst thing you can do.

After reviewing the supporting docs, the amount was reduced to $220,000 due to the type of employment of one of the borrowers. 

@Alex Ramos unless it was medically related, bad credit speaks to bad decisions made.

In this situation, I charge a $50 fee for the administrative time required.If your agreement was a reduced rent for one person, you should absolutely require a rent increase for the additional occupant.

(There is more 'backstory'... we intend to begin offering additional services like daily meals, housekeeping, etc, in the future, but for now, it's non-nursing, non-medical, simply standalone rentals.)