I only plan to manage these two from out of state until we're able to refinance our second home as we're losing money on this particular house for rent as we bought this home last year. 

And even a good PM will not watch your money like you do.

Mistakes I see people make is they plan on living there a short time and over renovate the property where they will never get the money they put into it back. 

This would be a waste of everyone's time and money.

Wouldn't it make more sense to raise money privately?

By managing yourself, you keep that money in your pocket.✅ Hands-On Experience – If you plan to grow your real estate portfolio, managing tenants yourself can teach you valuable lessons about leases, maintenance, and local rental laws.✅ 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.

Of course you can never have control of the money and you must have your QI in parcel before your sale completes. . 

Imagine making millions of dollars over the course of your career and then having to pay 30-50% every year to uncle sam instead of compounding that cash over time.This is exactly what real estate professionals have learned to mitigate.To reduce their taxable income, they just buy a building every year, do a cost seg, and use depreciation to reduce their tax liability dramatically.Their personal wealth snowball grows much larger and much faster than their W2 counterparts who give most of their money back to the government each year.Following this strategy as a real estate professional is one of best ways to end up with a much larger net worth at the end of your career.

Yes you will save some money by self managing but more important you will learn what it takes to manage a property. 

Joint ventures entail utilizing your own money to buy properties with others.