This negative equity position consumes the initial cash flow to re over the negative equity position.  

  (2) Variable cost: platform fees from Airbnb and VRBO, lodging/hotel/transit or whatever pass-through tax your local AHJ requires, cleaning fee, cost of replacement for consumables, repair and maintenance, etc. 

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?

.✅ 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.

Honestly, I wish more consumers asked this because there are far too many agents who believe their job is simply to show homes, write contracts, and collect a commission.

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. 

Google NMLS consumer access website.

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

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.