The nice part is, I renovated the whole thing in 2020(new shingle roof, new siding, new heating system, new HW tank, new kitchen, etc.) so I dont foresee any big CapEx expenses in the near future.

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. 

I even replaced old shingles and the 70 year old boards were in solid shape.

Shingles, 6x6 floor tiles, pipe insulation, countertops.  

@Jay Hinrichs  The dump trailers hold their value . and its so nice to back up at the landfill right next to a guy hand unloading shingles , open the gate and push a button .

Look for deforming shingles, if many of them are starting to fishmouth, meaning they are rising in the middle of their edge that can be a sign of age.3.