@Bradley Elrod  if you  rent to a family member at below market rent it is considered personal use. 

You need to seriously consider ditching this person and replacing them with a pro!

How would you pay the person if this is part-time help?

The entry-level Quickbooks Online software itself is expensive $250/yr... that's not even adding up potential books/courses, CPA fees or personal tax filing software like Turbo Tax.

Real Estate can be tricky to navigate but when you do it's one of the most fulfilling and rewarding Industries to work in. 

If they need any receipts/invoices, those are all in their portal.I personally would keep a spreadsheet to double-check numbers.

I mention this all because I personally recommend everyone spend several years (if not a lot longer) WORKING in real estate before trying to raise money from others.  

The Title company does  a search to see if the person selling has the legal capacity to sell, to find any  other owners, mortgages and liens on the property and to identify anything that may affect ownership to the new buyer.This is all done prior to signing for transferring ownership.It is not related to doing the Lease or the Option.Yes, the option fee is used as the down payment.

No "headaches" except for risk of near total loss of principle unless I put more money in...I'll take the risk of a project that I need to complete personally in exchange for a near-perfect risk/reward profile and complete understanding of the investment.

Very frustrating when I qualify for a HELOC but its getting stopped due to LLC vs my personal name.