I initially paid out of pocket for most of the interior updates / rehab costs when the family moved in, but now it could use new roof shingles (which we've got estimates on) and some minor updates in the kitchen and garage.

As you pointed out with your ac example, which could be a roof if you have shingles, or siding if you don’t have stucco.

I have a strong work ethic and don't shy away from hard physical labor thanks to my granddad making me carry pack of shingles up on roofs at 6am during my summer when I was 11 years old, my pay was dinner that night lol. 

Well........they sent a picture of a section of the roof, some of the shingles are u and guess what- NO insurance on it now.    

Just responded on PM, and the home was built in 1982, and the roof is made of asphalt shingle.

What type of shingles? 

Is market like Texas where they often have soil/foundation issues, or like MN/the Midwest where the asphalt shingles might have hail damage?

Thank  you so much in advance. can you further describe what you mean by "using as a business" big diffference between having company vehicles there vs. having pallets of shingles in the driveway. what specifically or how specifically are they using it as  abusiness

A short time after a hurricane blew some shingles off the roof and caused a leak.

There are some missing shingles that I was going to have a roofer replace once I closed.