First of all, do not take any money out of the business, because you will need it.

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.

Rents started to come down and I had to leave a lot more money in projects that I was in the middle of.  

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.

To answer your question directly OP, to sell a deal and make money. 

Quote from @Michael Overall: Good day, If an investor has 10 rentals and wanted to over time sell them and put the money tax free from a 1031 toward a large purchase is there a process to do that? 

We do have to come up with 40-60% of the LTV through investor money!

They make their money off of real estate agents, but real estate agents are the worst people to make money off because they are highly unreliable and in and out of the business when the market changes.Their target should be the consumer with higher levels that they can subscribe too for data, since Zillow is linked to the MLS now which makes their data somewhere more reliable.

I've never spent money on inspections/environmental before having the property under contract.

But do look at the shiny penny and spend big sums of money to learn.