Not having the correct team and systems in place and totally damage your reputation as a property owner/manager, if your team (the maintenance company) does not have the same vision as you.Perhaps there is someone out there and if so . . .

Also how do I make sure all secondary damage such as gutters, siding, windows etc are covered and accounted in insurance claim.

On another occasion I had them inspect the property after purchase and they informed me that due to the condition of the roof they were raising my deductible on any roof damage to $5K instead of the $2.5K for the rest of the property until I installed a new roof.   

Have a 1960s 30 unit single story motel where we are coming up on some end of life issues: the cast iron plumbing is disintegrating underneath bathrooms, radiators are starting to leak, electrical is in poor condition, and just today, discovered significant termite damage affecting multiple rooms.

You have to do lots of damage control in that buisness and be a strong negotiator. 

Did it lead to more damage to the furniture/property and end up lowering your ROI?

Does Builders Risk cover any damage caused by an occupant prior to getting them evicted?

We use a spreadsheet to track any deductions for issues caused by tenant damage.

A new tenant might not pay rent, need to be evicted, do damage etc. 2.

We’ve had to replace two window sashes (tenant damage) over several years, and it was so easy to order and replace just by having Lowes order it by the actual number, was only like $125 each time.