& Buyers (Crypto Holders) are responsible for volatile currency that will cost a premium but will be instantly converted into cash.Middle man, in this case a broker/realtor cashes in on premiums from seller before the home is even listed.

Preqin dataBenefit #2: Private Real Estate has Low Correlation to other Asset ClassesThe goal of every portfolio is to create the highest total return with the least amount of volatility.

I'm trying to think of a way I can find them properties that will give a good return (Since the stock market has been so volatile) and take a slice of the pie for doing so.

In Chicago, the market is much more volatile than most of WI, thus risky.

Considering it all together with your equity build up and cash returns make the deal significantly better putting your money in the stock market (especially with the current volatility). 

Furthermore, another reason why many people claim real estate is better is because prices are not volatile.

That's why it's important to choose more stable markets that don't have a lot of volatility in pricing.

Naturally, I too am more inclined to house-hack as @Aaron Lee suggests, but despite if you are able to find a relatively new duplex at your budget, it seems that you'd be putting yourself in a potentially unnecessary volatile situation. 

Volatile markets like these (houses under $75k) are being over paid for with commercial notes lasting 3-5 years by investors drastically underestimating unit turn costs. 

Baltimore's market is way more volatile than the DC market and people who are investing in Baltimore know that they are taking a larger risk than placing capital in the DC Metro.