I'm cashing flowing $300+ on the two I have currently. 

you can achieve a lot more than 1 house per year. what is your starting cash position?

However, it did not perform well overall and barely cash flowed (although, to be fair, it was on a 15 year note). 

I've posted to Zillow, FB Marketplace, and Avail (and therefore its syndicate sites) and have had lots of views and saves on the Zillow statistics, but only one inquiry/tour requested.

I agree with you about how he needs to get refinanced in 3-5 years so I can cash out.

We’re interested in cash flow and recycling our money.

However, I just reached the decision to sell it an hour before posting this (so that part of the process has barely started).I have an eye on a specific property I really want, but it just went up today and already has 32 saves on Zillow.

Currently, I'm only offered 27 hours of work per week at an average/below-average pay rate, which isn't nearly enough to save for a down payment or qualify for a loan.I've tried selling belongings to generate extra income, but it's not sustainable in the long run.

Being a first time home buyer as well as having the home be owner occupant I was able to only put 5% down through money I had saved throughout high school. 

Any market and any property can cash flow.