What I'm hoping to find: I'm hoping to make connections, for mutual benefit; this could be investor friendly agents who have experience with identifying promising house hacks, investors who are looking for an additional financial partner, investors who are looking for a partner to help manage the load of projects (I am naturally drawn to planning and execution), and more broadly anyone who is willing to share experience and create new connections!

Next StepsContact 311 or the Chicago Department of Water Management to request a meter recheck or usage audit.If the new bills seem drastically off, request a review for billing errors or adjustments.Consider installing low-flow fixtures or monitoring usage with a smart meter device to ensure there’s no hidden waste.It’s frustrating, but you’re not alone in this!

That brings us to 2- the ability to negotiate to CREATE a good/great deal3- financial staying power (being able to survive when things go south)4 - property management 5- creativity 

You need a reserve to handle unexpected costs, particularly during the first 1-2 years of ownership and learning how to manage the property. 

It looks good) I stumbled across someone locally who does it, but I'm sure you could find someone there if you or other out-of-town investors like the idea of paying a bit more for that level of security and obtain a remote monitoring source of the exterior of the properties.

Building a strong team (agent, contractor, lender, property manager) is key—seek referrals from experienced investors.

If numbers work and risks are manageable, this could be a solid house hack!

Others not including their management fees in returns to enhance returns, lots of questionable ways people calculate returns but many avoid to say "what did the investor actually make". 

Quote from @Duane Williams: We’re a family-owned fix-and-flip company operating in San Antonio, TX, and Northern Virginia, managing everything in-house—from wholesale acquisitions to rehab & construction (with our own project managers and crews) to listing & selling through our licensed brokerage. 

It’s impressive how you took this single-family fix-and-flip from start to finish, self-financing and managing the project as the GC.