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welcome. go to as much networking events as you can and mingle. there are great posts on this forum which you can learn on many different topics. the podcasts are great. if i can help in anyway, reach out

If you need to cover utilities, the numbers tighten significantly, making a lower purchase price essential.Let me know if you have any further questions or want to explore these numbers in more detail—I’d be happy to help! 

Are there specific tools, presentations, or approaches that help them feel more confident in taking that first step?

Good thoughts as we embark on this New Year.....our time is precious and should be valued way more than most people do.One of my favorite sayings - "Money is a replacable commodity, time is not"

Chicago, with its vibrant neighborhoods and strong rental market, is a prime location for this strategy.

Any tips/pointers, etc?  

This is assuming the way you notified the tenants of the new rent was considered legal notice in your market. 

I'm a pretty handy guy but this would be outside of my realm, but my experience helps me understand how much this type of improvement should cost.Improvements: remodel kitchen and bathroom, paint interior, fix exterior scafolding.How should I go about finding a contractor?

Absolutely, I am taking great pride this year in making content that is not microwaved from sourcing a few google articles that "gurus" just reguritate.