If you’re feeling uneasy about the potential headaches, you might consider a local property manager who specializes in room rentals or shared housing.

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.

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

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.

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?

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

See Listing Link here.I am attributing a lot of the "slowness" to the season. 

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.  

Make sure your accountant specializes in real estate taxation.