Ask to access some equity and deduct from the sale amount.

The repair cost will probably be less than the deductible, and who wants a black mark with the insurance company?

Do you deduct cost from security deposit?

If the board doesn't follow the bylaws, then the board and/or the association might be legally liable for your damages.We have a $20K deductible for water-related claims before the master coverage kicks in, and an owner's personal insurance would cover the deductible.

You should establish a minimum amount of coverage (building limit, deductible, Liability, etc.) and then request quotes at that or better. 

From this book, I took that business trips such as travelling to go check on your houses  are tax deductible.

You issue the form and deduct his "share" as an expense.

If you cease to occupy the residence as your principal residence for a continuous period of one year or more, the interest on your mortgage loan may not be deductible for Federal Income Tax purposes."

Where homeowners would pretty much make you whole, less deductible, if you have, for example, a broken pipe, flood insurance coverage is much less.  

Other factors that will impact are the Replacement cost of the building, the deductible chosen, Liabiltiy limits used, construction of building, age of building, etc.