Are there specific tools, presentations, or approaches that help them feel more confident in taking that first step?

@Julie Doke: Industry specific software speaks to you and you can easily relate it to your day to day process.

Honestly, I never fully understood what they meant—until recently.I’ve been diving into some larger-scale real estate projects, specifically in commercial properties and multifamily development.

I don't know your living situation but if your paying x,xxx for rent or a mortgage and instead by living in one side and renting out the other you will be paying y,yyy instead and y is less then x that's great, especially if you can rent out your primary residence and make income there too. 

Specifically, I would encourage you to continue to seek local opportunities for equity growth as well as seeking out-of-state or upstate opportunities for cash-flow (i.e.

Speak with a real estate attorney about the legalities of wholesaling real estate in your specific area, the internet isn't the place to get legal advice.

Bit of a crossroads here, I'm hoping someone with a similar situation could chime in.  

If you've been in similar situation, have you found it brings an issue down the road with future tenants or current?

Proportional leverage (like 27% LTV) isn’t specifically required, but if you don’t reinvest the full amount or fail to replace debt, the difference will be taxed as boot.

Here's how to handle your situation for tax purposes based on IRS guidelines:1.