There's plenty of question that each rabbit hole could offer.

I have ran into a few holes and wanted to know if anyone had any ideas.

That is, if they all went down in value by 10K, you'd be 40K in the hole with mortgages. 

Sell the money pit do not keep trying to fill the hole.

You have a square peg / round hole situation which is always tricky in insurance.

People hate conflict.....so they ignore what they should do because it can be "messy' and hope for the best....and then seem shocked when the outcome is 100x worseYou don't have to be an a-hole to handle this in a professional, tactful and friendly way......but it should be handled, not ignored

The flower bed had weeping holes for excess watering; the water would drain out and leak into the drainage system in the middle of the garden. 

You’ll get paid every month no problem but might have a few holes in the walls.

For me, I only allow my partners to pass on "economic shares" (I am NOT a lawyer, I might be calling this the wrong thing), so their spouse will still get the monetary benefits of the partnership but not have any decision-making power unless I vote them into the company, it prevents me from becoming parnters by default with someone who may not know/understand/value/think/share my investment philosophy5.

The location of those holes for the vents nails correlate with where the leak is inside the attic (which as stated I caught before it did damage to the ceiling of the house).