@Tessa Mac You can certainly rollover your old 403b plan into a self-directed account. 

It offers features like Automated rent collection (Tenants can set up auto-pay) and you can receive payments directly into your account without any manual tracking.

I recommend finding a tax strategist who specializes in real estate taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

How much cash should I plan on pulling out of my own bank account for this?

Always keep personal and business accounts separate, document all transactions, and consult a CPA or attorney to ensure compliance and maintain liability protection.This post does not create a CPA-Client relationship.

Outsourcing the 3000 would cost me .277 more per piece but that doesn't take into account my time, wear and tear on my equipment, 3 trips to the post office, making a total mess of my office, etc.Put another way, knowing I can only do about 40 per hour tops times the .277 per piece I save by doing it myself, comes out to $11.08 an hour.  

Keep in mind that if issues arise and you decide to sue someone, it may be more challenging to take legal action against the wholesaler and hold them accountable for their actions.

Absence fraud, the success of the limitation will often depend on action which regard the entity as separate from the individual and other entities; separate bank accounts, attention to organizational structure, filing of entity documents, non commingling of funds, etc.  

They also memorialized my account when I protested them not memorializing my mother's or my uncle's who have both passed away. 

It's important to consult an attorney and an accountant eventually, but your first step should be to discuss your plans with your lender.