In investing, you need to take risks. However, being a successful one, you know the risks and can prepare for it.
You make some good points. If it doesn't quite cashflow, maybe that's good. With rent appreciation, mortgage ammortization, and property appreciation, maybe it is worth the "negative" cash flow. A 1% gain in value in a year on a 50k property is only 500 dollars, while an increase of 1% on a 200k property is 2k. That's like another $125/month in theoretical cashflow. I guess it could go down just as much. (Sorry, I'm thinking out loud and working this out.)
Looking back at my analysis, my budget usually breaks with the property management 10%, where I would be paying myself. I would still have enough for expenses and budgets, just nothing left over for me. A possible plan could be to manage it myself until I am able to get a positive cashflow out of it due to a refinance or rent increases.
I have to do more thinking on this but maybe this is what I have been missing. Maybe this market is too rich for cashflow, but great for appreciation.