I spent thirty years handling title insurance claims and can state with certainty, mistakes can be made by the most experienced searcher/examiner. 

What can I punt to the property manager and what should I be handling? 

They do the title search (yes, they use a title company), create the deed, handle the invoices (paid repairs to property get credited to either seller or buyer), and conduct the closing and deed recording.I've heard it works differently in other states.  

He has a master's degree in taxation and can handle the most complicated situations along with the easiest and you will learn about investing just by talking to him. 

I assume travel to view the property before buying, closing, meeting property management companies and potential tenants, handling any serious tenant issues, but what else?

Here’s the monthly income and expenses:Unit 1 (1/1) - $800 (Yearly Lease, legacy from purchase)Unit 2 (2/1) - $1200 (6-Month Lease)Unit 3 (1/1) - $900 (Yearly Lease, up from $700 at purchase) Total Income - $2900Mortgage P&I - $1076Homeowner's - $157PMI - $182Property Taxes - $183Water - $86Internet - $60 (needed for security cameras)Gas - $103Garbage - $42Landscaping - $47Total Expenses - $1922Cash Flow - $978Going forward, I’ll be using a cash reserve to handle any vacancy, CapEx, and maintenance costs.

How do we handle and get this contract!

Only OP knows his family dynamic and if they are family that can handle financial interconnections or not.

You msy consider calling your locslhousinh authority, the ones who handle the Section 8 program Even though you may not want to use the program, it could open your eyes.I  have done this and been suprised at how much they pay....or how little.PS.

Finding a property management company that you can trust with your investment can be a weight off of your shoulders and provide "mailbox" money to you without you having to lift a finger (except for when you have to grab that money from the mailbox).The cost of property management services varies, but any great trustworthy property management company can outweigh the cost substantially by providing you with time-saving services that handle the day-to-day operations of owning a rental investment property.