Individual roofer with only medical coverage - do I hire or not?

[Nick Brubaker]

Hello,

I have a rental property (sfh) that needs some roof maintenance.  I got a couple recommendations and a couple quotes, both offering the same scope of work and warranty.  One is an individual with only personal medical coverage asking $700 the other is a small company with general liability and worker's comp asking $1050.  

If the individual is working alone and would be covered medically if he were to get injured is it reasonable to go with him?  Could I go with him and mitigate liability by having him sign off on some kind of waiver?

Thanks