I don't delegate bookkeeping for security reasons.I finally realized that at this time in my life, it is much better for me to pay a bookkeeper. 

I would just feel like a dead weight and once they has the info they could ghost me. 

If one of them are staying than we keep the security and tell them that they need to figure it out themselves.

This should transfer the weight of the room to the new support as the seasons change.  

How should the security deposit be managed in this transition?

Given your experience and strong financials, you have some solid options:Commercial or Portfolio Loan: These are tailored for investors and can help you avoid personal guarantees, especially since you have an LLC.BRRRR Loan (Buy, Rehab, Rent, Refinance, Repeat): Some lenders offer BRRRR-specific loans with funding for purchase and rehab, allowing you to refinance based on the new ARV once stabilized.HELOC or Cash-Out Refi on Current Rentals: Tap into the equity on your single-family rentals to secure funding for the 4-plex purchase and rehab without high origination fees.Each has pros depending on your cash flow goals and timeline.

And need an LLC to initially secure a lender as well if going that route

I feel like just about every month, I see RE investors with 1-2 year's experience starting a new fund and advertising on Facebook for LP's, as well as the daily "JV deals" that straight-up violate securities laws.

By leveraging my knowledge of the transaction and timing, I negotiated favorable terms, securing a rare townhouse investment opportunity in Charlotte’s historic Fourth Ward.

By leveraging my knowledge of the transaction and timing, I negotiated favorable terms, securing a rare townhouse investment opportunity in Charlotte’s historic Fourth Ward.