Some people use dynamic pricing such as price labs and the built in Airbnb tool to set their pricing.

Kurt makes an excellent point . . . the market is very dynamic currently with interest rates and inflation rocking the buyer's boat. 

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

If one doesn't have dynamic needs, then just focus on that specialty. 

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. 

I don’t necessarily think STRs are a shortcut, despite being a fan of them.We bought in late 2022 (we weren’t naive to the market dynamics/timing, we simply finally had the down payment at that time and it serves as our vacation home as well).We put 10% down and probably cash flow $500/mo, but hard to fully say as we are just now entering busy season.

Compared to Vegas and there is hardly any land left so you wont see the same dynamics to Vegas as you did in the Crash..

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

But, this assumption is not necessarily prognosticated upon any dynamics - just static $$ assumptions.