I have properties in Fairfield, West end, East Lake, and others, and they can cash flow but the management is difficult (as in getting cash collected from tenants).

That someone you hire is your biggest risk and it is essential you find someone reliable.Research as many people in your local market that do the work you need and talk to them on the phone.

After analyzing over 1,300 active single family homes in Reno, Nevada we found that the majority of homes cash flow around a 4% cap rate, with outliers in the 5s and even some at 6%.A cap rate is a measure of a property's investment potential, calculated by dividing the property's net operating income (NOI) by its purchase price.

They can come to the table with cash to make up the difference.

These are park owned homes that generate really solid cash flow. 

I am not sure who you are using as your Realtor but I would reach out to a Anthony Wong who specializes in investment rentals or buyig the right primary that can be converted to a rental that will cash flow.

I would say it is on life support because after refi the negative cash flow necessitates extra reserves.

Another alternative that gives you quicker access to cash would be to borrow against it now.  

I'm okay with risk, but with each added piece, the idea makes less and less sense to me.STRs are an absolute cash vacuum in year 1 (and 2 in many cases).

And finally (I personally despise this option) you offer cash for keys.