Are you using any visualization tools like Tableau?  

why, don't you install video surveillance system, that way you can get a visual of someone coming into your property!......

Not that it would matter at this point but I would think with a visual inspection (some use a telecscope like device to see it up close from a distance to give general ideas about roof) a good all around inspector maybe would have been able to determine the multiple layers.I Was looking at your first picture of the front of the house and the edge of the roof where it meets the gutter in the front looked like something was going on there.

It lets you easily create your floor plan in 2D and 3D so you can visualize and plan how you want to change/renovate the space.

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It's strengths are aggregating visual content, either uploaded by you or "Pinned" from other websites which could be your own, but predominately are others.

Bottom line, You never really know what to expect, but if you can get into the habit of visually looking at everything yourself (heck, take pictures for later reference, I do!)

As a designer, I like the visual interface of tenant cloud, with the widgets and integrations. 

They have been very professional, knowledgeable and smart, and imo, don't even visualize themselves as having any kind of a deficit.

@Emily Beatty Just to add on..... any chance the lender/appraiser would be willing to use FaceTime with you or your tenants in the building to get current, visual access plus any specific measurements?