They need a well-designed workspace, ultra-fast Wi-Fi, and long-stay conveniences like a washer/dryer and a fully equipped kitchen.Why This Matters for Your ROI:When your STR feels tailor-made for a specific type of guest, it stands out in a crowded market—leading to higher occupancy, better reviews, and repeat bookings. 

If the trust gifts you the property, it retains the original cost basis, potentially leading to high capital gains taxes upon sale.

This can be a great way to get leads on off market properties.

From my experience, security has been good, there’s plenty of space around the pools and clubhouse area too, so it’s never loud or crowded, and the HOA appears to also cater to a broader more modern and contemporary audience, to include its Canadian, Brazilian and European guests and investors.

Unless you are an experienced investor like Alan, it often leads to higher costs.  

This leads to Early Issue Title Insurance being a requirement of the buyer's lender, leading to higher closing costs for the buyer and the seller having to document the following:1.

.✅ 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.

This can potentially lead to problems and the safety of the others in the home.I am planning on speaking with him about the lease violations and switching him from yearly to monthly with an increase in rent, due to the increased labor of the cat and the checks in of the cleanliness of the room. 

I suspect maybe something like Hagerstown or Cumberland, which yeah are Class D like markets with declining populations, high drug problems, no strong job base which leads to non paying tenants.

This experience proves that even with challenges, strategic renovations and persistence can lead to a profitable outcome.