I found myself in a similar position to you about 10 years ago.

Rent out our current house (likely $5k/month) and use a home equity loan on the primary residence or similar financing to purchase a home in Seattle.4.

I wanted to solicit some background info before reaching out to my accountant and she advised similar to your comments. 

Once you move to Chicago, look for similar groups—Chicago has a vibrant real estate community.Building a Team: Since you’re new, connecting with a knowledgeable real estate agent, lender, and property manager in your target area is critical.

If a PM handled similar situations, they would be using their HVAC go to technician, they would take a certain % of the total and add ontop of it for themself, parts would probably get marked up, it would be like 3x. 

I've written similar posts a handful of times, and there are other threads in these forums that discuss investing in Japan.  

JMHO  I use a similar approach to paint sheen.

@Gregory Schwartz Believe California, Colorado, Illinois, Maryland, New Jersey, Rhode Island, and Virginia have similar laws.

Look at Homes.com or Realtor.com to get an idea what that type of property is selling for (look at the ones Pending or Under Contract)...or, look in the county's GIS system to see what similar properties sold for.Once you have an idea what a fair market value would be, let the landlord (if they're interested in selling) mention their price. 

Dennis' dad and I actually tripped over something similar back in Chandler.. we learned to tap into city planning websites and even call the permit offices directly to get a real sense of their backlogs.