So I'm focusing on durability first, but it also must be visually and functionally appealing to a tenant. 

They also have the kitchen designers at the store so they can help you with measurements and visualize your order.

I would always inspect a HUD home yourself or have someone you trust inspect it visually before offering.

I'm not looking for instagrammable moments, per se, but the visual appeal is incredibly important.

A visual inspection and a pressure test should uncover most issues. 

You are what you think about.Face the fear and act.Common Sense + Action + Persistance + Humor + Visualization of Success = Power, do not lose your power.Print this out.

and only after you covered properly the "other" aspects of risk management (insurance, umbrella insurance, proper property management, etc.).Here are some visual diagrams to help you in your quest:Asset Protection Decision Diagram - to help assess the need for asset protection, and what to implement : https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-decision-diagramAsset Protection Onion Diagram - what, when and at what cost one should implement in terms of asset protection - https://www.biggerpockets.com/files/user/CosIorg/file/asset-protection-onion-diagram-v2What is needed for a complete asset protection OR the domains that need to be intersected to find asset protection

Had this landlord visualized his decision in this manner, he would have never done this. 

I am assuming you are buying an older property since the majority of buildings in Chicago are 100 years old, in that case, it's unlikely the garage would have anchor bolts.I lean on your inspector or get someone out there to visually inspect the garage. 

Does anyone have an Excel modeler that helps visualize different buy/hold, BRRR and flip partnership structures/returns?