The challenges in real estate teach you invaluable lessons that you might not gain otherwise.I also invest in Chicago, so I have a few thoughts in response to the questions you raised.

You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.Good luck.

Randy, thanks for your response. 

Only an investment team can provide the crucial local knowledge you need.Moreover, you'll need various resources to find, validate, inspect, renovate, and manage a property.

If this is a single family, they are responsible for pest control.

I am only familiar with the contract in my state but items seller agrees to do based on inspection findings are their responsibility unless spelled out differently.  

Look for undervalued properties.Network: Connect with local real estate agents, contractors, and other investors for insights and deals.Analyze Properties: Use the 1% rule to evaluate potential properties (monthly rent should be at least 1% of the total investment).Secure Financing: Explore different financing options like conventional loans, hard money loans, or private lenders.As for timing, if you can handle the extra responsibility, starting now could give you a head start.

You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.Good luck.

Quote from @Dan Attivissimo: Thanks for your response, Jonathan!

Buying an investment property at 21 shows amazing foresight and financial responsibility.