You will have to do it after each time it rains. 

Sure, strange things happen but, if there's 30-40+% chance of rain one day, "we" aren't doing a re-roof then!

Rain water leak happened on one unit where these tenant issues happened.

It sounds like he has assets that you could go after if he doesn't pay any judgement you win. 

For example, I bought a property that had a judgement lien that was about to expire if the plaintiff took no further action.

@Nina PenuelaOne of the things we have seen, specifically in Ohio and Indiana is local building authorities target out of street owners with ridiculous fines and make life miserable.Had one where the porch light was out and charged a $50 fine.Another one claimed grass was not cut because it rained for 1+ week and did a $400 fine.

We have a judgement against the tenant in county court.

I’d rather trust a professional with a moisture meter to see if it’s dry (just after or even during a heavy rain would make me feel better) before fixing the ceiling.

They should be able to sue you and your daughter in Michigan and then record that judgement to enforce in Illinois if needed.

You don't know any roofers, so you just pick one out of the yellow pages (yeah, I'm showing my age) and they got 1/2 way done and then went to do another job and it rained, destroying your roof?