.✅ 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.

Private money and personal funds.

While personal loss is difficult and understandable, running a business that directly impacts property owners requires a contingency plan.

Me having several thousand good reviews help, but personally I would not book a property with 0 reviews. 

suggest you think of using digital business cards, but not typical ones like all solutions out there, something that is the first AI-powered digital business card and offers AI persona, which handle client questions and would act as your 24/7 personal assistant. it’s called Avatalk,

If you close with a conventional loan, it will need to be in your personal name.

Quote from @Jessie Dillon: just my 2 cents.. i'm not a fan of the syndication model. there are better ways to invest more passively where you have more of a say in what goes on, can achieve higher returns, and can have your personal interests at a higher priority. 

A person files for and get's whatever from of welfare.

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.