At one point years ago, I toyed with the idea of owning giant apartment complexes in multiple cities.

We don't like the idea of owning in WA anymore.

You can contact some local property managers and get a better idea of the rental market.

I love the idea and its really quite nice because the costs are minimal and upside is huge.

That said, even with conservative rental income estimates, my living expenses would eventually drop to several hundred dollars less than what I’m currently paying in rent once the house hack starts generating income.I do have cash reserves to weather some rough patches, but the idea of pushing my budget this hard makes me uneasy.

I don't think you're being too ambitious, I think its a very smart Idea especially in Chicago where there are an abundance of 2-4 unit buildings!

I will not comment as to the tax laws and underlying rules - that is a discussion you can have with your tax advisor who presumably you are paying to help you.What I will do is provide practical and business guidance on tracking time.Firstly, there are apps available that can assist with time tracking where you can specifically detail your time, who you met with, etc.

I was curious to learn more and liked the idea of niche diversification outside of my current active real estate business.

Some lenders offer creative solutions, like a cross-collateralized loan, where they use your existing equity as security without refinancing the duplex.Another idea is partnering with private lenders or exploring a second-position mortgage, depending on your lender's terms.

They usually sound good, but give very little practical advice and make it sound easier than it is.