I'm not trying to insult you, but the terms "36-Unit Multi-Family" and "First Time Investor" should not go together.

I would go with a combo W/D unit just like @Greg M. mentioned above.

He's seen me grow to four units (3 properties) and I'm thinking, there's gotta be a guide or book that would help him just follow step-by-step how to rent out his existing property and buy a new one.

Hi, Working FT and finished renovations on a 2 unit home.

Our HOA/complex manager has saved my butt more than once when a guest has locked themselves out of the unit and I'm across town or whatever.

How did you learn to build that level of trust so early in your career?

In this market i would only go that route if you have the resources to cover their initial investment so there would be no loss of capital if things go bad.One of the syndications that i am an LP buys MF, rehabs the existing units, converts tbe garages into max number of studios, brings all units to top of market rent, and exits with max NOI.  

House-hacking in a multi-family unit is one strategy I wish I had been aware of when I chose to purchase my first property.

So to help cover expenses and see some cash flow would focus on multi-unit property. 

Lenders will allow you to use 75% of the rental income in a 2-4 unit.