For example, I didn't see one home with catastrophic roof failure (though I'm sure some are out there) but at most I got glimpses of plywood here and there with lost shingles and underlayment. 

All:I have ~30 properties/50 units and seem to have to replace shingles on 2-3 roofs every year, not to mention the new roofs I have to put on properties that I acquire. 

Luckily the price of the roof has to do with more than the shingles, which can be replaced with reflective white.

The owner must grant such access to computerized orother electronic records & to any computers, facilities & mustprovide any information or assistance needed to access the records.5.

My lawn company cleans but they don't always do the roof so it sits on the shingles, which can cause issues not only to the shingles but eventually the decking and interior attic area ( I presume so just like standing water on carpet will do damage) - so now I'm making sure the lawn guys look up on the roof to make sure it stays clean.So this "moisture" that was detected or presence is being taken care of to ensure there is no escape into any part of the house if that is likely.The test they did though showed no evidence of anything in the home.The tenants were presented with a settlement or buy out or what ever the language of the day is for them to leave and guess what......they had their own air quality test performed and they paid for it and that company also said there was no mold in the home.My PMs did an inspection and they are changing the air filter and keeping the home very clean.So now they are staying presumably until the lease end.Geez!

Also will need shingle repairs and painting some time in the next 5 years since in HOA.  

Is it interlocking shingles?

There may be a broken window, 3 steps going down without a handrail from the porch, 2 shingles blown off by the wind.

That is a gable roof with a three tab composition shingle which is the cheapest shingle on the market.

Simply put, you drive around neighborhoods looking for distressed properties (Boarded windows, uncut grass, missing roof shingles, etc.) and write the addresses down.