Find a duplex or place with a suite and rent that out (or live in the suite and rent the main house). 

Sadly I understand the stupidity in the system and always put full stars like my "Auto Order of shampoo" was as amazing as the "Hotel stay where they upgraded me to a suite and gave me free room service" simply because the line was long and I had to wait all of 10 minutes (I wasn't upset or even had a stern look, they just offered).

Interior highlights include an indoor-outdoor living room, a master suite with a private balcony and a screening room with a hidden bookshelf door that accesses a secret bedroom.

Landlords often get sued, and when they do they don't want the target of that suit to be an LLC that owns real estate with significant equity. 

With that what we have moved to is civil suites for failure to perform on contract, seeking not just contractual monies owed but also damages from failure to perform including legal fee's, getting a judgement issued and then following mechanisms for wage garnishment. 

They each have the preferences but if you explain to them exactly what you are looking for in terms of protection they can suggest something that suites you.As for the questions.1.

But Portland market did not see that massive price drop.. it did on some high end luxury sfr product and there was some deals on Lots over in Central Oregon..

No house is perfect and it is a matter of know what needs to be fixes vs what doesn't suite your taste.

I know other states are starting to allow for these types of units more commonly, including adding "in-law suites/flats" which would include their own kitchen, bath, etc; however, IL has seemingly been pretty slow to change.If you have a couple lots in mind, feel free to reach out and I could do a quick check to help you determine the likelihood of getting something like this done.

New furnace, windows, flooring, modified the floorplan for a more open kitchen and a master suite.