I currently have a majority of my savings invested in the stock market but am looking to diversify into real estate and other ventures to achieve my financial goals.

I would get an attorney or title company involved to create your loan documents to ensure they comply with the law and cover all the aspects you need.Another method that is likely your best bet to take on investors is to create a joint venture (JV).

Here is a solid example you can adapt for a joint venture (there are differences, beyond just nomenclature, for a partnership and a joint venture): https://templatelab.com/joint-venture-agreement/Again, I would caution use of this document without a professional to review it.

If I pay it off, I could maximize cash flow earlier, reducing financial stress and allowing me to focus on other ventures or simply enjoy life more.On the other hand, I know some people advocate for keeping cheap debt and using the extra cash to invest elsewhere for potentially higher returns.Why I’m leaning toward paying it off:Security: No debt = peace of mind.Financial freedom earlier: A fully paid-off rental would give me a significant monthly cash flow?

This is a new venture that I'm looking into and real excited about. 

who are involved in wholesaling or other real estate ventures.

Buy and large I manage these rentals and we think of it as my side venture, not his.i already have the LLC but my tax guy won't file the rental in the llc because he says I need more than one rental and probably a Different kind of business entity.

I am looking to switch CRMs and was wondering if anyone has REALLY DIALED IN their workflows in REI REPLY that they would be willing to share. 

While to some extent software can act appropriately based on averages, that'd different than actually understanding the marketplace and workflows and optimizing.  

It sounds like you navigated the challenges well and gained valuable lessons for your next venture.