My gut says you probably want/need separate policies for the different entities at the very least - the purpose of having them is to keep things separate in case of a lawsuit, so combining insurance would pierce the veil and allow someone to come after everything. 

None of these originators are allowed to assess you as a higher risk because you paid off a mortgage early. 

They had allowed two months to go by without paying their bill.

Criteria:6 months STR2 bd, 2 ba, Single Level House Furnished with yard, washer & dryer with A/C (inland not near coast)Pet Allowable 40 lb labodor 10 yrs, 40 lbs Red Heeler Mix and 6 lbs catNear VA Hospital, shops, grocery stores (at least 25 minutes commute)

I remember I use to try to convince owners to allow section 8 in the Greater Pittsburgh market because, as you said, rents can often be much higher and from my personal experience, the tenants were often better, longer term tenants because it was hard as heck to get on the section 8 voucher program and even harder to find a place that accepted it.

This made the overall appearance of the property much better and allowed us to re-sell for a profit.

In each instance, fault was on person B (Yourself in this scenario) and NOT on person A who the tree trunk was on there property but limbs overhanging neighbors, AS LONG AS they had readily allowed and made no conflict to person B cutting out/down whatever was projecting onto there property line. 

Most HOAs do allow rentals but you may need to obtain a rental permit or adhear to certain lease provisions.Feel free to PM me if you have any questions - would be happy to chat / give guidance

Get a powerful router that allows creating two accounts.

Some employers, (when you're 50+) 401k adoption agreements will allow you to do an "in-service-rollover".