@Angelo Darin technically speaking you would borrow the money as a "business venture" and that business would pay it back over time from positive cashflow.The interest on the HELOC would be a tax writeoff for investment purposes - you should speak to a tax professional about this.

My parents had rentals when I was a teenager.A combination of talking to my mom, interest rates and life made me buy my first purpose bought rental. 

Now, some of the math here might be dependent on how you PURCHASED the property (with cash or with a loan) but just for concept purposes here's what I would say the differences are:1.

I have a professional property manager (PM), who sends me a monthly statement detailing all income/expenses and will send me a form 1099 for tax purposes.

It may be a good home for a first time homebuyer - but it's not a good buy for investment purposes.  

The second an agent is involved you are defeating the purpose if the agent does any work i.e. agent gets compensated.

To you it may mean something different, but I truly believe the way this video should be understood is as follows (at least this is how I took it).To genuinely have decided to start (to take that first step) with the purpose of genuinely intending to finish at that goal.

and I have to answer "yes" to this.It's never a good idea to purposely be a slumlord.

I plan to draw monthly amount later down the line for myself to be able to quit my job and am not sure if I would need to create a LLC and file my earnings under a W2 for tax purposes.

This strategy can work if you are just looking to scoop up a few properties, if you are looking to scale up to more than say 5 properties, you would probably want to look at building new purpose built duplexes, quads or multi units.A new duplex would generally rent for around $1600 / month for the main floor and $1000 for the second suite plus utilities.