2.The best way to obtain the necessary permits and ensure compliance moving forward?

I went to school in Santa Barbara and moved from just north of San Francisco to live and invest in Reno, NV. 

Starting with house hacking is a smart move, especially in a higher-cost area.

I've only evicted a tenant through the court system three times in the last ten years, but I remove about a dozen tenants every year outside of the court system, all legally.Any tenant can move out in two weeks.

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

I started with single-family homes and then moved on to condos, typically holding onto properties longer than I probably should.

Most likely due to wanting to invest his time more wisely:)If you can move in with family or friends RIGHT NOW and rent out your house and start DIY managing it BEFORE moving out of state, that would be best.Otherwise, handymen, cleaners, agents, etc. are highly likely to take advantage of you once they find you you live OOS.

My plan moving forward is to acquire another 20 doors before years end and I'll provide another Portfolio update around then.Happy Investing!

@Paul De Luca PITI 11.4k, Gross Income (once I move out) 12.5k 

Sure, all channels can work, even seller financing or foreclosures, but in my experience, a well-connected agent can uncover hidden gems that often outperform the trickier avenues.Since the post is still fresh, I’m curious.. do you foresee other potential add ons that might elevate the returns even further, like corporate housing partnerships or short-term seasonal leases?