You can mitigate your self employment taxes.

@Adam FrancoFlips are recorded at your regular income tax rate, subject to self-employment tax.You figure out your final cost basis (purchase, rehab, insurance, property taxes, financing, permit fees, commissions, utilities, etc.) and the difference between the sales price and the final cost basis is the profit made that will be taxed as ordinary income.You should speak with a CPA to help organize things and try to minimize the tax impact.

I’m just hoping for a little advice or some out of the box thinking that would help me with my self-inflicted predicament.

Looking at a small 24 unit self storage business on 2.5 acres in our local industrial park.

Are you trying to manage it your self?

The tenant would need me to be the bank for them due to them being self employed and not  showing a strong tax return year after year.How would you structure this so everyone is protected?

The plan is to self manage and continue with the short term and long term rentals.  

Anything to streamline the process and create a self-propelled system is what we want here.

With all the training, self education, and books that I have read, the reality is that I need a second set of professional, experienced  eyes to go over the numbers with me.

Setting up a self directed IRA might work for you as well.