@Kole Kingslien  Guidelines for land contract:- Payoff of Installment Land Contract Requirements When the proceeds of a mortgage loan are used to pay off the outstanding balance on aninstallment land contract (also known as contract or bond for deed) that was executed within the12 months preceding the date of the loan application, Fannie Mae will consider the mortgageloan to be a purchase money mortgage loan.The LTV ratio for the mortgage loan must be determined by dividing the new loan amount by thelesser of the total acquisition cost (defined as the purchase price indicated in the land contract,plus any costs the purchaser incurs for rehabilitation, renovation, or energy conservationimprovements) or the appraised value of the property at the time the new mortgage loan isclosed.

If you report as a Schedule C, it won't hurt you, if you are a corp it will hurt you because it gets deducted before you get to your bottom line which goes to you via a K-1.To quickly address the 401k component, if you're reporting as a corp, the employer portion of the contribution will hurt you and the employee portion will not hurt you since it is on your paycheck stub.Not sure exactly how it would work if you have a 401k AND you report on a Schedule C.Of course, I would talk to your CPA about this further.

That will and should have a significant role in your planning.Also, like @Gino Barbaro mentioned, you need to define your funding strategy.

Here is the the IRS audit guide which explains the different methods - what I am calling a "mini" cost seg study is defined here as the "residual estimation approach": https://www.irs.gov/businesses/cost-segregation-au...

Cash flow is only one component. 

However, I was hoping to get more applicable thoughts from you locals.I will admit, though the units I have identified do cash flow enough for my needs, I am concerned about the appreciation component of condo's in that area.

How to define it is hurricane damage.

In Utah there is documentation that should be signed either way just to define the relationship. 

I am now under contract to purchase a triplex using my VA loan with a tehab component, where will will live in a great home in one of the most desirable neighborhoods around, while renting out the two units in back. 

What is the current condition of the property's structural components?