This rating will give you a sense of the carriers financial solvency.

Are you certain you would have to sell at a loss?

Regarding total potential loss, Umbrella is better.

The only question is if the increased risk of loss is worth the extra return. 

While Stessa is great for cash flow tracking and NOI insights, it lacks the structured accounting needed for tax reporting, loan applications, and long-term financial accuracy.If you're scaling and have multiple properties and business entities, double-entry accounting ensures every transaction has an offset, reducing errors and making tax prep smoother.

This approach focused on limiting potential equity loss if the LLC were to face a lawsuit or liability claim.

House hacking is financially a no-brainer and no city in the US (including Chicago) has more duplexes than Milwaukee.

So losses from that specific rental may be utilized.  

Moving forward, we’d like to unload our rentals and move the proceeds into syndications, however, we do not have the accumulated losses to offset capital gains/recaptured depreciation for our rental properties.

You are correct passive losses can only be used to offset passive gains.