Is this question stemming from a funding issue like an FHA loan?

Then you need to get a decent loan for the balance, very hard in the cannabis industry.I love the ambition but I recommend starting a bit smaller to start.

And lastly....The biggest issue between PMs and owners (regardless of relationship) stems from unexpressed expectations. 

You can invest more than the capital gain realized if you wish, but the interest will be bifurcated solely for 1400Z-2 purposes and only the interest stemming from the qualifying investment will be eligible for the OZ tax benefits.All capital gain: LT cap gains, ST cap gains, 1250 gain, and collectibles gain are eligible for qualified treatment under 1400Z-2.If you are thinking about a QOF investment, I'd advise you to onboard a competent tax professional as an external partner on your team. 

But the short, I'm in the cannabis industry in Colorado and concerned big/local banks will deny me a loan. https://www.biggerpockets.com/forums/22/topics/801783-colorado-cannabis-industry-and-getting-approved

I've heard stories in the past of other industry employees getting rejected and having to find private lenders etc, however, that was 2015-2018...and now in 2020 the industry is steamrolling forward in rapid growth, so more and more cannabis industry workers on W2 must be applying for home loans, especially out in CO. 

Two years or two tax returns stems from the period outlined in the safe harbor or rev proc 2008-16 and referred to in a couple case rulings as two years, two calendar years, and two tax years (appropriate times not recommended or required times). 

My own two cents from the world of tech entrepreneurship, the fact hat you have demand may stem out of your ability to sell, not necessarily from a great product. 

While it may cashflow now, my concerns would be higher maintenance costs and tenant quality/stability issues that stem from the overall functional obsolescence that's present in a lot of Chicago's 100+ year old housing stock.

Time to get educated and learn how to stem that trend.