Hello - I have a somewhat unique situation that I am unsure how to best claim on our jointly filed tax return.

While private money isn't highly regulated at the federal level, there are subtle nuances to be aware of in each state that may trigger your loan becoming a security and then the SEC would have regulations to consider.

The IRS allows 1031 Exchanges to defer taxes on what they consider to be capital assets. 

*The taxpayer or RPE attaches a statement to the return filed for the tax year(s) the safe harbor is relied upon.If I don't meet all the 4 bullet points for Safe Harbor am I still able to take the Qualified Business Income Deduction for a profitable Rental Property?

I have 2 rentals and do use a CPA for my tax returns. 

Still need to get my taxes done this year for them.

So, right now I am trying to decide if I should start working with Tax Sentry, Inc., a CPA for my business and personal taxes.

Bottom line is that you may put yourself in a situation where the best way to maintain your tax efficiency is to keep your investments foreign for the long term. 

Any current roadblocks including time-to rehab permits being issued, local landlord laws/trends, property tax to rent YoY trends, etc. 

Why didn't you simply elect this LLC to be taxed as an s corp, rather then forming a new entity?