My recommendation would be to increase your deductible to a level just below painful, have your properties 4-point clean, consider your FICO because providers will, and shop coverage. 

If you spend time learning how to manage well, your income will increase, you'll save time, and you'll maintain your sanity with the courage to expand.

In some homes planting the front or placing pots could increase the curb appeal, in others it could be paint or furniture etc.

Yeap, exactly same as Zillow's Zestimate increased the price of houses.

As rental rates increase, cash flow becomes strongly positive.  

I told subsequent tenants this once I moved out of that unit and have never have had a problem since.

All the fine print came in subsequent e-mails.

After that's under control, focus on increasing income through additional work at your current job, taking on a side hustle, or finding ways to increase income on your existing rental.At the same time, educate yourself.

The Raleigh market may have increased by 40% after the Apple announcement, but it wasn't because of Apple, at least not solely.

So what kind of property would it take for you to increase your cash flow by $2000 - $3000 a year.