This picture is not super helpful to answer your question but if I were to guess I would say you either have no flashing or older wood bevel flashing outside and the caulk has dried out.

Lying on mortgage applications is bank fraud and can trigger severe financial penalties, prosecution and prison time if convicted.

Few others are saying mortgage owner needs to be named insured and otherwise the bank won't agree.The owner is the LLC and should be the name insured, and you could add yourself as additional insured.However, as the mortgage is under your name, the change of the name insured may trigger some issue with your lender and a due on sale clause.

More than likely the sale amount triggered a reassessment-price went up-it happens all the time.

Does it look dry rotted? 

However, when it was time to pull the trigger THEN my mortgage company tells me I no longer qualified due to the income from the property.

Like dump it on the floors, let it absorb in the wood, and then we covered the floor with a plastic drop cloth to keep it from drying out.If that doesn't work, you may need to sand the floors.

Worry about the paperwork after you pull the trigger.

If none fit it likely will be a dry well for your criteria-I dont invest in Michigan but I've heard Detroit is booming.

The cash flow has been phenomenal but the well has dried up in terms of new affordable properties to buy and rent out.