@Robert Lei, nope, don't do it.We manage hundreds of doors and we have a set policy; we will not rent to a contractor, nor will we hire a tenant to do work, even if it is in a different building than where they live.Reasoning:  a tenant is a problem, and you can deal with just this one problem. 

Yes, transparency is a good policy here.

It's just your ability to tolerate risk. 

Depending on the policy they would only have to pay the deductible to have the roof replaced which is a win / win.

At the end of the day, the way I look at it (since this is my housing cost too) is I would be spending $1500+ minimum to live this quality of lifestyle and if I can get that number low/close to zero, I'm winning.

You can have your agent give you a list of the problem breeds for your policy.

Licencee & Investor (Zeroed In)

They will most likely need some training on how you want them to run the place, your policies, quit and pay, etc... 

My regular insurance policy covers rent loss, but only in the event of a catastrophic occurrence  ( fire , flood, etc). 

Plus, you really want to co-own a 4-unit that only has 3 tenants in it to make it cash flow with someone who has zero real estate experience?