I am here to create a business strategy that protects personal and business investments and mitigates risk,  procure a coach or mentor, and set up tax strategies to create long-term wealth for myself and my family. 

Personal Guarantee: Will you require this?

Which is very complex and costly and likely warrants professional help.Now, if it's just you and your spouse, then your 2024 tax preparation is likely relatively straightforward:- you will create a Schedule C on your personal tax return- you will NOT report any costs of purchasing the property or its rehab, not in 2024- you will report your business overhead expenses such as marketing, driving, technology etc- you will end up with a business schedule showing zero income and some expenses - not breaking the rules but potentially raising an audit flagCan you do it yourself?

A contract is only as good as the person enforcing it.

Whether the seller was open to a buyer commission or not, I wouldn't put an additional cost into any personal purchase.  

I typically don't comment on other's businesses unless I know from personal experience.

For instance, said property manager manages maintenance issues, problems that arise during bookings, basically anything that needs a physical person at the property, while I manage the rest?

I'll let others chime in on their experiences, but from a motivational perspective, I think attending live events and getting the "conference high" is something that only happens through in-person connections and being in the same room with investors who are eagerly pursuing their real estate/financial goals. 

This is what I heard third hand, so not sure if it is true but i believe the person got this from the PPM which was noting where the monies were going. 

.✅ 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.