The biggest pain points like others mentioned is the Pre-Payment Penalty, Lender protections, and undisclosed fees. 

Right now, Stayfi has been beyond a pain!!

You can do the same, find the pain point and solve it.

If buying a condo research the HOA health, engineering study, last 5 years of HOA board and meeting minutes and last three years of HOA financials/reserves. 

I have lost one in the past and it was a total pain in the butt when the tenant moved out...

Does anyone have any pain points / challenges that they'd love to share?

What I do worry about are the growing pains as we transition from a full-blown capitalist society to whatever is next.Because before goods and services will be so abundant that they are free, they will first have to get gradually cheaper and that forces businesses to compete through more  automation and less human labor in an accelerating cycle.

Pain points that I'm not yet aware of in this space, that I can potentially approach differently/with a new perspective.

You get better with time, you learn from painful mistakes more than from your successes, but that's when you become like Jonathan and tell other people it wasn't that easy.

The Detroit Health Department even reached out to us personally last week to begin working in tandem with us and our in-house property management team placing section 8 tenants for them that are in dire or desperate need of shelter into our properties.