How does your insurance company know you need to fix the roof?

Plus the learning curve to invest effectively was too steep to completely disregard it. 

Background info: A tornado came through about a year ago and tore up the carports for a rental property of mine in Iowa (I own one unit in the 12-plex).While the carports have been rebuilt, the HOA's building insurance is coming up for annual renewal with a VERY steep price tag.

-Has no crawlspace (common for older properties) so we couldn't see the foundation-Drywood termite/wood decaying fungi damage seen on all the windows/doors/parts of the beam on the exterior, parts of roof decking and rafters in the attic-Old leaks/moisture damage seen in the ceilings and attic-Parts of the roof has patch work-Roof doesn't have any permits on record (don't know how old it is)Seller's offer to me:-Fumigation treatment for drywood termites (tenting the house)-Replace and repair all damage wood throughout the house-Replace the entire roof with a new permit-Replace one window in every room (not all)-Pay for a structural engineer to inspect the foundation-Offer to get quotes for repairs and have a 15-20K budget to make all repairs, house is 500K.

I purchased a 3/2/2, 1366 sqft rental home built in 1986 (roof 8-10 years, no pool, smoke alarm, etc) in May 2023.

New roof, solar, paint, lvp in the living room, granite countertops, cabinet handles, fixtures, carpet on stairs and upstairs, refurnished entire house.

Having 100 units under one roof gives you far more focus and economies of scale when it comes to maintenance etc.All your risk is concentrated on one pile.

If any of you could help me determine what kind of property damage I should avoid either because it costs too much to fix or it is just too difficult/ time consuming (things like termites, gas lines needing repair, roofing, etc.).

So how are banks, lenders, and investors navigating the turbulent waters to mitigate risks and seize opportunities.Banks' Resilience and Caution: Despite reports of office towers selling at steep discounts, major banks have managed to dodge significant losses in the face of mounting defaults.

The  unit is rented consistently and is functional but also needs upgrades, new siding (has 2 layers), Some rooms could benefit from re-wiring and more insulation,   Painting is always an issue as it is not plaster but older thin wallboard. kitchen is fairly new, bathroom could use upgrade, upstairs bedrooms have some pitched ceilings but I don't think based on the foundation/construction it is a candidate for a full second story and it had a new roof a few years ago.