So, even a small negative like a $50 unpaid cell phone bill that goes to collections when you switch carriers tanks their score.

This creates a negative initial position.

Why would I be cash flow negative and losing money for years and years?"

When I ask for clarification, I only get vague responses.I’d really like to hear if others have gone through similar experiences with AppFolio.

Negative CF, which is what you are describing, means you are buying your property, and making no money in the process.

Is there some reason that you or the company simply don't discuss what happened and use this as an opportunity to turn a negative post into a positive one for the company?  

For this deal to work under those conditions, the purchase price would need to be closer to $179k.With your original assumptions 249k, the deal is marginally acceptable but not great, given the negative cash flow in the early years.

Yes you can find properties which you will be able to purchase, but ROI will be near zero or negative. 

As a community I think we should focus on helping people who have had their housing situation negatively impacted recover as quickly as possible.

I invite you to perform the exercise and find what your cap ex allocation should be.certainly $50/month for maintenance/cap ex and misc is not enough and this property is definitely cash negative when properly allocating for expenses.