Her deployment (not sure the deployment is short term or long term) was last month and asked me to allow her son and grand children to stay and she will continue to pay the rent.

- I would select a market that allows you to purchase a cheap (under $150,000) single-family in a C+ or better market.

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

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. 

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)

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

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

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

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".