You may very easily spend over $500 in legal fees, court costs, and administrative fees in order to collect that additional $500.  

If the former, who has authority to enter into a purchase contract and convey title and what steps, if any, do they need to take in the estate administration process prior to or concurrently with the sale of the property?

The only real risk comes from a "ready, fire, aim" approach, or a disregard for the fact that rules do in fact apply.The key is to think of yourself as a fund manager, and keep your role administrative in nature.  

LOLBTW, Trusts are not the best business structure as there will be limitations as to deductible expenses in administration for a small operator.No entity protects you from liability from your management or activities that you are engaged in, insurance takes care of that.

Some lenders will advertise a low rate and points but make up for it in "junk fees" (ie: underwriting, appraisal, administration, servicing, etc...).

Your 401k money is safe and yours, but administratively it can be a bit more complicated to get the signatures required to release funds to you in those scenarios.401k funds would not help you with a 203k buy/renovate loan.  

I took a few college courses on business administration, as I would like to be my own boss in the real estate world, and I have a few close contacts with some local real estate agents however that's as far as my knowledge goes.

The IRA component of a self-directed plan is the same as any other IRA when it comes to administrative issues like contributions, distributions, rollovers, beneficiaries, etc.  

Two items I did leave out is agent fees for tenant placement contracts and administration/accounting which will later will be minimal, so I guess these two items should be more than covered in the $10,000 misc. right?

As an agent you will learn the entire process, contracts, escrows, title, financing, business administration, accounting, people skills, etc., there's no better training for getting into investing in real estate.