Capital raising lead generation tools, email templates, automations, and automated processes.

What worked for me was focusing on building strategic relationships with top tier people (quality partners) who could complement what I brought to the table—sales, management, and execution.When you are approaching sellers for creative financing, leading with a clear value proposition (and CONFIDENTLY) is key.

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

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. 

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

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.

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.

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