Liability Protection: Transferring to an LLC provides asset protection but may not always be worth the hassle or cost.Next Steps: Review your loan agreements, consult your lender, and get advice from a real estate attorney and tax pro to ensure everything’s compliant and beneficial.

I have been consuming as much education/reading regarding out of state investing as I can as well as literature regarding buying larger buildings (not quite the syndication level) although I have been reading that material as well to digest.

An LLC offers some liability protection, BUT states vary with the cost to get and maintain an LLC.

So you have bad financial terms working against you along with finding properties, making deals, getting financing etc Secondly - for me it's time consuming.

.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

Unless you make the theme of the house around that famous person, I dont think consumers will pay a market premium on ADR to stay. 

Or judge always protect tenant?

The question that I ask my clients is why would you only want to protect your principal of you investment? 

It is very time consuming to get permit approvals and you may be in a position where you need to extend, pay fees, etc.. when your loan is past due.   

An LLC when properly formed and administered provides separation and protection of assets that are outside of the LLC from the actions of the LLC.