There is a market I want to expand into but need to find a piece of land. 

If you have a busy schedule or the project has a lot of pieces, paying for that smoother ride can protect your profit more than it hurts it.

I've done over 200 fix and flips + new construction and I've never laid a piece of tile and have no intention of EVER learning that skill or ANY of those skills. 

Buy a larger piece of farm ground.  

Don't forget the basics, buy property for less than what it's worth, not just because you are getting just a little money down.In negotiations, break everything down into pieces.

I believe he has done some updates on some of the key pieces I felt I needed to understand though.  

That can still be fine if year one you’re living in one unit at a big discount and the tenant is helping you pay down the loan.The key piece is what you’re counting in that “net.”

Cash-on-cash is definitely the piece I’m digging into next because that’ll make or break whether this one’s worth moving forward on.

Tennessee’s rules and your net-worth gap are exactly why you want the legal and tax pieces talking to each other instead of using a one-size-fits-all S-corp answer.If you’d like, I can outline a “model structures” I use for couples in similar situations (pros/cons, how income and liability flow, etc.) so you have something concrete to discuss with your local attorney and CPA.

And if I didn't understand the financing piece of real estate then I could have gotten stuck with properties with really high interest rates that could have made many of my properties negatively cash flow for a long time.