I'm working on building mine with the hopes of eventually dumping my current property manager and curious to hear from others:1.

You'll eventually build enough income from rentals that you can quit the W-2, or you can stick with it and keep growing.Passive income?

Markets I'm interested in are the Chicago suburbs, Milwaukee suburbs, Las Vegas, and eventually Los Angeles when money permits.

My goal is to leverage my wholesaling experience to learn the ins and outs of the industry, and eventually scale up into more complex investment strategies.

Building a strong team—like a trusted realtor, lender, and eventually property manager—will definitely help as you scale.

I am considering buying a quadplex as a house hack, but the eventual goal would be to move back into my current primary residence rather than buy another, so the seasoning period for me to get another loan would not apply.

Going to a meet up is good you can get the local perspective from other investors, but eventually you will need to take action.Depending on your goal you could partner with someone who has done it before or find a team that can help you.  

Yes, eventually we want to buy more rentals (not back to back, but within the next 5-10yrs).

And eventually, they also fail financially, because over time capex exceeds cash flow.So I am very much in favor of @Tim Ryan 's idea: pick a market and grow roots.

Don't buy or transfer ownership before he passes to preserve the step-up basis eventually when you inherit.