They make their money off of real estate agents, but real estate agents are the worst people to make money off because they are highly unreliable and in and out of the business when the market changes.Their target should be the consumer with higher levels that they can subscribe too for data, since Zillow is linked to the MLS now which makes their data somewhere more reliable.

If you ask a banana farmer if bananas are good for you, he will tell you they are absolutely necessary to a healthy diet . . . and he happens to have some he can sell you.You asked if you need an LLC.

And, at least for me, there always seems to be either someone that is willing to make pennies on a flip or someone like my builder partner, who can always do the work for so much less than I could, that he can pay more for a property and still turn a healthy profit.Thank you the insight.  

I am responding as a consumer not a STR owner we had one its lasted for us for exactly one tenant then we felt it was too much work for the return  on investment we do much better loaning money and buidling new homes than to worry about people goofing up our homes :)I do have some MTR you know fully furnished homes in Vegas and those are money makers for us top of the line tneants paying double the going rate for rent.

.✅ 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.

The seller must've been very motivated to retire...are you buying any residential properties now or does this project pretty much consume all of your attention these days?

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. 

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

Time ManagementReal estate can consume all your time with endless tasks—client meetings, marketing, and paperwork.

Google NMLS consumer access website.