With a dynamic real estate market, diverse neighborhoods, and high rental demand, Chicago is a fantastic place to invest in house hacking. 

There is always risk, and these are highly risky and regulated techniques.

I have experience in single family fix and flip, 1-4 family rentals, small apartments (10-30 unit), 100+ unit apartments, development, commercial retail, industrial and office.

I mention all this to in short say, expect very high maintenance on the front end. 

And your net worth will thank you.If you still want to go ahead, you'd be better off buying a house than an apartment because, while the value of the building itself will go to 0, you'll still have the value of the land, bearing in mind that the land might actually lose value too given the depopulation and the yen depreciation.Sorry if I'm pooping a party but make sure you understand what you're getting into (which you're already doing by asking the forum) and then make the decision that's right for you according to your objectives.

In-person interactions are great for building trust with potential investors.Real Estate Platforms:BiggerPockets: A robust platform for connecting with private lenders and investors.Fund That Flip, PeerStreet, Groundfloor: Online platforms connecting investors with real estate projects.Social Media Groups: Facebook and LinkedIn groups dedicated to real estate investing often have private investors or lenders looking to connect.Personal Network: Often overlooked, but friends, family, and colleagues may know individuals interested in investing.Private Money Brokers: If you're working on wholesaling deals, you may find brokers who have established relationships with private money lenders.Real Estate Agents: Some agents have connections with private investors, especially those focused on investment properties.For your 50% LTV, it's good to approach investors who may be interested in lower-risk, high-equity deals.

Granted this primarily filters out the small deals or the highly leveraged deals, neither of which I do, but making 20% on a ARV 150k house is $30k. 

PM fees are high, exactly because so much work is required in managing STR.  

I'm working with a company who owns a small, 19 unit, senior and low income apartment building.

Case Study: A Successful Joint Venture in Real Estate - An investor identifies a distressed property with high potential but lacks the funds to purchase and renovate it. - The investor partners with a private lender who provides the capital.