I use to  give estate planning seminars with an attorney and stock broker, so I know it's not that big of a deal.

Unless you have a solid plan to turn this around, selling now and cutting your losses might be the best move.

With the exception of building a trailer on the property (these are hard to finance), this sounds like a good plan AND if you are using it for your business AND your business pays more than 50% of the rent (if you have more than 1 tenant), then this is a more financeable property in the eyes of banks and credit unions as it would be consider a commercial "owner-occupied" property. 

Just wanted your plan to be realistic.

I am currently 36 years old and planning to start my real estate investing journey this year.

.✅ Hands-On Experience – If you plan to grow your real estate portfolio, managing tenants yourself can teach you valuable lessons about leases, maintenance, and local rental laws.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ 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.

You need to make a written plan with him to get this over the finish line, with cost estimates.

Thirdly, financing and potentially selling later on could be challenging again with the part of the plan being on a campground. 

I dont know the delivery time on a ADU but I'd assume same with site plans and zoning. but how do you get your money out of that?

Hi Perry, getting an LLC would be smart if you plan to scale your portfolio.