@Adam Poffenbarger are you self managing? 

Are you self-managing or paying a property manager?

For real estate just start analyzing as many deals as you can so you get more comfortable and confident.

I have had people tell me they like the property, though, so I'm confident that I'll eventually be able to find people.

Since rent range is pulling from property managers the data is cleaner, because so many self managed property investors market their property way too expensive and they will never get that rent, it is just hopes and dreams.

Then plan and design how you're going to deploy that cash via what strategy your wife and you have confidence in.I use a excel or google doc and my first sheet would layout all of the details of the sale including all costs that go into getting closed.

A team of lenders, title companies, contractors and RE attorneys, and significant knowledge of the intricacies of real estate transactions, you will be MORE than prepared to dive feet first into your first deals and will do so with CONFIDENCE.

If you go back to work as self employed, there are some NonQM programs out there that can do a cash out refi after just 1 year of bank statements or P&L. 

If you self manage I would still keep property management cost in mind if you change directions. 

Why did you decide to self-manage this time instead of giving it to your property manager?