I'd like to understand which is the better option between these two and the reasoning behind it. 

Hey guys I'm looking to buy a 2nd property in the L.A area and I want to know what the better strategy would be: 1. sell my primary residence and buy a duplex so I can do a house hack OR 2. do a cash out refinance to house hack for said duplex.

Used PSI last year, they did a bad job, the snow wasn't even bad last year and with several attempts asking them to do better within the terms of the contract, they still sucked. 

Current job sucks, new one could be better?

Asking in the correct forum will get a better response.Read the RULES!

Would have done better if not slowed down by COVID in 2020 Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I'm seeking to be in an environment with like minded individuals to learn and network to grow my portfolio and eventually network to collaborate on larger deals once I have a better understanding of the commercial side. 

.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

Question 3: Is there a better way to protect property besides an LLC, such as a trust of some kind? 

Yes you partner with them on the individual deal but you get the reps in to become better at watching a deal from start to finish.