I only spoke with one person so far and they scheduled for more information gathering/ rental investment calls from them this upcoming week.

Quote from @Daniel Windingstad: Quote from @Obed Calixte: Some people have the personality, processes and systems & time to self manage, some do not.

They are all under my personal name.

This deal proved to be the perfect balance of financial gain and personal enjoyment.

Overall I would personally consider how I can still grow with the freedom that I have focusing on my real estate.

I financed the acquisition of the land with personal and private money.

Personally I wouldn't feel comfortable trying to wholesale a relatives $1M home knowing that I am breaking the law if I cross over into doing anything that can be considered representing them in the transaction, and knowing it will only be marketed to people who buy properties wholesale (typically investors who don't want to pay retail prices), instead of the majority of retail buyers active in the market who are typcially willing to pay more. 

.✅ 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.

Personally, I advocate for a long-term investment strategy and would recommend investing the funds, provided you are comfortable with the expected return on investment over time.

I personally use 40% but I'm also in a higher rent area.