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?

It would be like if someone prepared to sell by painting to create fresh visual interest, but chose fuscia and lime green...those colors would certainly catch the eye but I'd never claim that they overdid the curb appeal by painting with too much visual interest.

This image comes from the book "The Visual Handbook of Building and Remodeling, Third Edition" by Charlie Wing (available on amazon and other places I'm sure) (The Taunton Press, 2009, Newton CT) It's a great book which I'm sure can answer your question regarding more research. 

I'm a visual learner so this definitely helped. 

I have a hard time visualizing things myself so using Alex has been a god send, here's her website https://www.cheatsheetdesign.com/ It's around $400 for her help and personally is worth it to me just to save my time!