It can be time-consuming and challenging if you try to do everything on your own, so partnering with a trusted team can make all the difference.

All the various consumer laws exist specifically to stop bad actors from doing stuff like this. 

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.

We discussed this in an earlier post.Obviously, if loans are being made without any provision in the Operating Agreement, it’s time to get in touch with your State Securities Protection Division - usually a part of the State Attorney General Consumer Protection Agency.

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. 

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.   

Hello, it is really time consuming for me to analyze each property by manually entering its data to calculate the return.

Also, are you meeting with a "consumer" lender or a "commercial" lender?