We then refinanced the property and it has given us $140k in cash back and continually produces $1,800/month in cash flow.

There are so many ways to get started, I have trouble figuring out what is best for me and my circumstances.

Recently (last few years) time has not been an enemy as RE pricing has been appreciating higher than the cost to hold, producing net gains for holding longer.

We then refinanced the property and it has given us $140k in cash back and continually produces $1,800/month in cash flow.

Anyway to trouble shoot this?

If property management costs $40,000 or $80,000 per year, you have to ask yourself if you're willing to stay put and keep working for that amount or if the beach is what really calls you.As others have said, it's a seller's market so you may want to consider selling at least some of the properties and investing in something that produces a better return with less effort.

I would say the only people that will go for that deal are:1. dont know any better2. have a very troubled property and just want to exit any way possible. or you buying in an area say like Gary Indiana or some other area were there are thousands of vacant homes.

Back to your point, we are in a hot market with more demand than supply on the renter side, but for me my vacancy is not driven by lack of demand (okay one property was a trouble property to rent), but it was just the downtime for turnover between tenants.  

Should I expect trouble keeping it rented out?

I originally did my calculations with the rental calculator, but I was having trouble getting the numbers I needed.