This resulted in us being able to purchase a half million dollar multi family complex for about $3500 down.

A multi-family could work but he says if he is going to buy he want to at least break even and not have to pay.

https://members.digonline.org/events/Details/dig-general-meeting-creating-a-multi-million-dollar-rental-portfolio-67422?

I became a supervisor there with no college degree and geld the position for 4 years. 

For example, I bought a commercial lot that bordered a commercial lot on one side and MCD lot (allows multi family) on the other side.

Use the $180k as a 20% down payment on a larger million multi-family property.All of these options feel viable and executable, but is there an option that I am missing and what are things to look out for each option.

We are looking to purchase our first investment property to get the ball rolling and are leaning towards 2-4 unit Multi out of state as we are in Ca. 

Offering your services is advertising and is not allowed outside the Marketplace.

My backup plan is to purchase more condos (~200k/each) which gross about 45k/year (net just over half that) and save up until I can afford something bigger.Ideally I want to stay in the same city with the multi and do a combination of long term and short term rentals.Thank you for your time.

Would I just continue to buy one house at a time or would it be better to try to scale up (larger package of sfh or small multis) I work a steady job and my strategy right now is buy and hold.