I allow adding tenants as long as the existing tenants are in good standing.

But there is a way that you can still do a 1031 and sell them individually.

Seems like too much work for too little return UNLESS you own the property, or perhaps have an option to purchase the property allowing you to capture any increase in value.   

I love that you have specific goals for 2025 - I believe if we think it, write it, say it, and share it our goals are 10x more likely to come to fruition.Are you able to do option 2 and just house hack a 2-4 unit building and use a renovation loan which allows you to put down 3.5-5%I highly suggest getting to some local chicago meetup groups (we have an in person one on the 17th)...here is BPs list: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a full list of the chicago meetups that I can share with you too if that'd be helpful.

Based on a quick answer from Perplexity it seems like there would be no issue with you buying the home and collecting passive income, but you may not be allowed to manage it yourself since that is considered active work.

There will likely be a partnership return required where you flipped a house with a partner and lost $120,000.If you sold the other property within the same partnership, it will also be reported on that partnership return.The net result to you is that you will receive a K-1 showing your income / loss which you then use to report on your individual return.If you made no money within the same year, you likely pay no additional taxes / get no additional refund.Best of luck.

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

My retirement system doesn't allow for me to roll anything over given that I'm still employed with the company and also under 59.5 years old.

As you said, this allows you to track LLCs (locations) and properties (classes and/or customers).

You would still save more money 9 out of 10 times living with your parents but being able to leverage a low down payment loan will allow you to get a very high ROI on relatively safe investment.