Have an open conversation with your relatives and let them do most of the talking.

Unless your relative or friend is lending to you at a reduced cost. 

Take them to your relative and see if they are okay or if he needs corrections.

It depends on your (and your relative's) risk profile. 

Your relator should be able to tell you how/if you can add this as a contingency.

You have feet on the ground with your relatives so perhaps one of them can be your PM.

While I agree renters insurance may cover this if it is a known problem and it is documented I would tell your relative to call and see if they will pay expense. 

IMO and experience the biggest issue isn't your relative staying in her home but planning for her economic future with assets left to her and no income.

I’m honestly also subjective on this topic threadssince being a Wisconsin residentIf I was living somewhere else I would consider per Marco advice Indiana , Wisconsin , Texas and possibly Carolinas for leveraging your moneyMaybe have your relatives / old associatestake turn taking exterior photos every several months( beside solely trusting property manager pictures)Make sure you keep eye out for building code violationsProperty manager email you his/her photos ever few months( repairs of work started / completed )Give local police district your telephone number, so you notified of any issues at the propertiesVisit your potential properties maybe at least once every 3 months ( spring , summer , and winter )Approval all marketing your property manager publishCollect rent on-line for tenantsAlways have several exit strategies

What happens if one of your relatives made a decision and now you are ponying up money to cover it.I love real estate.