If I don't understand the fundamentals of the terms myself, how can I confidently approach the topic.

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.

That would not give me a lot of confidence that they will continue to be long-term tenants.How confident are you on your market rent projection? 

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.

Be confident! 

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.