If you are having an insurance inspection done, they'll most likely just walk the outside of the property so clean up any obvious things like trip hazards, broken roof shingles/tiles etc.

I’ve seen several posts on social media where they’ll be a downed tree on the property, a few shingles blown off by wind, or some damaged siding, and the poster always says “it’s not always passive”.My question is: what does everyone do with their monthly repair costs?

On an early 1900s house slate is common and will last a long time but it's hard to find someone to repair and more costly due to lack of materials. 3 Tab shingles would be next and are very similar to what is available now with improved designs in the dimensional shingles which oddly enough were made to resemble the old slate shingles.

I agree with @Sarah Kensinger.You should just hang out your own shingle on this.

I often buy several water heaters or large batches of shingles when they are on sale knowing I will use them within a year or 2. 

If shingles are broken or missing, leaking, rotting, etc, that's a defect.

The roof was so old that most asphalt shingles were down to just the base fiberglass base material.  

I had 2 - 30 yard dumpsters brought in to hall out the plaster and the old roof (which was like 8 layers of shingles).  

Once you remove the shingles, theres a good chance you might need a new layer of OSB.

Things where deferred maintenance is 3 to 5 layers of shingles, bad furnaces- you name it.