Who is responsible for repair

In our association, if the roof leaks and causes damage to the home owner's ceiling, the Association is responsible for repairing the damage to the ceiling, even though the ceiling is owned by the home owner.

If the siding on the building leaks and causes damage to a window (which is owned by the home owner) wouldn't the Association also be responsible for the damage to the window?

Our Association is arguing that the windows are the home owner's responsibility and it doesn't matter how they were damaged. Would this position hold-up if challenged?

Unless the roof leak or the siding leak was caused by some specific event, i.e., not lack of proper maintenance or repair, then these are not insured damages.

As to who is responsible, you need to read your documents very carefully to find out who pays for what. It usaully gets down to what is the unit and what is the common elements. If a common element defect allows water to damage the unit, then one might assume that the association should pay for repairing that damage. However, this may only be the case if one can show that the association was neglegent by not properly or effectively performing it's maintenance responsibilites.

My insurance company would only cover the damage if it were caused by a single event (hurricane, ice storm, etc.)