Anecdote: There was a brief time when I took a break from tech project management working for software development companies, and did a brief stint as a project manager for a small handyman startup in the real estate business. I ran my own handyman company for beer money in college, sold it after college, and have seen the handyman services industry grow and evolve with technology. It's been very exiting to watch.

The work itself was a cakewalk. Dealing with property managers, contractors and laborers was less of a cakewalk, but still manageable.

Where I saw an opportunity for the RE business I worked at for two years (because of business decisions now even the owner has admitted were not just stupid but "f--king stupid") was to try doing exactly what Latchel is doing for property managers. We had all the resources, we had the people, we had the market and we had the local reputation to actually get two management groups with over 20 buildings interested enough to say "Show us your proposal and we'll take it to our owners".

That idea died because of someone high above and their ego, and even though I eventually returned to tech[1]--I still wonder what it would have been like had I pursued this exact idea on my own.

Good luck Latchel, as other comments are showing here: this is definitely much needed, and if you do it well, congratulations on your future riches, heh. The demand for this is HUGE.

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[1] Me, returning to tech after two years in real estate https://www.youtube.com/watch?v=LJ5nV9aKthU

Edit: If you ever start operations in Chicago, or plan to, I can likely make some introductions to a couple of large property managers I have a good, personal relationship with that may be interested to at least hear your pitch.