Hi southernsibe,
I think, as long as this is going to be an occasional 'personal favor' type thing rather than A Business, probably the only thing I'd do would be to have an honest talk with my insurance carrier. They should be able to tell you what waiver might be useful or necessary, and how it should be worded, and what they will/won't cover you for (although you might make sure to press for 'and are you CERTAIN about this? is there anyone else I should talk to?
).
In regards to the likelihood, high or low, of various demographics being inclined to sue, remember that it is not always a person's individual decision. Health insurance carriers quite typically require you to give them the right to sue or not sue as they see fit, so if someone gets hurt and the family needs insurance to help cover the costs and the insurance company goes looking for someone from whom to recoup... you know?
Obviously people are often incautious and get away with it (I myself jaywalk far more than is good for me and am still here). However I know of someone who lost everything, and I mean pretty much Every Darn Thing, through being sued by someone's insurance company for an injury that occurred on an uninsured property (and 'not covered by your policy' is pretty similar to 'uninsured'). I also know someone who was boarding horses without the knowledge of the company that carried her homeowner's policy, and when they found out, coverage was cancelled, leaving them virtually unable to get any other company to cover her but if she didn't get replacement homeowners' then she was going to lose the mortgage and thus the whole property. (I never did find out how the story turned out). So Things do sometimes happen. Something to think about.
Good luck, and I am optimistic you will find that your homeowner's carrier has no major problems with your idea,
Pat
I think, as long as this is going to be an occasional 'personal favor' type thing rather than A Business, probably the only thing I'd do would be to have an honest talk with my insurance carrier. They should be able to tell you what waiver might be useful or necessary, and how it should be worded, and what they will/won't cover you for (although you might make sure to press for 'and are you CERTAIN about this? is there anyone else I should talk to?

In regards to the likelihood, high or low, of various demographics being inclined to sue, remember that it is not always a person's individual decision. Health insurance carriers quite typically require you to give them the right to sue or not sue as they see fit, so if someone gets hurt and the family needs insurance to help cover the costs and the insurance company goes looking for someone from whom to recoup... you know?
Obviously people are often incautious and get away with it (I myself jaywalk far more than is good for me and am still here). However I know of someone who lost everything, and I mean pretty much Every Darn Thing, through being sued by someone's insurance company for an injury that occurred on an uninsured property (and 'not covered by your policy' is pretty similar to 'uninsured'). I also know someone who was boarding horses without the knowledge of the company that carried her homeowner's policy, and when they found out, coverage was cancelled, leaving them virtually unable to get any other company to cover her but if she didn't get replacement homeowners' then she was going to lose the mortgage and thus the whole property. (I never did find out how the story turned out). So Things do sometimes happen. Something to think about.
Good luck, and I am optimistic you will find that your homeowner's carrier has no major problems with your idea,
Pat