It is slowly rotting and needs significant repairs to get it prepared to sell to a typical home buyer for a primary residence.

You'll also want to make sure you have your full team ready so you can be prepared when the right deal comes along. 

Seller financing can be a fantastic way to get into a 4+ unit property, especially in a competitive market like Chicago.Have you started reaching out to owners directly or networking with agents who specialize in multifamily properties?

A tax advisor specializing in real estate can help you navigate deductions, plan for 1031 exchanges, and ensure compliance with ever-changing regulations.

I started my career working for Marriott in New York and Toronto, specializing in dynamic pricing and maximizing revenue.

You can also search for local FB groups that specialize in longer term stays.

My thoughts:- best advice above is to get a good attorney that specializes in evictions. - Who ever told you that only 30 days notice is required does not know CA law.  

Find an architect who specializes in this type of work, and who is very familiar  with the building department

Make sure your accountant specializes in real estate taxation.

I would actually recommend using the agent finder for the market your looking to get started in to find you an agent that specializes in out-of-state investors in your chosen market.