Any positive cash flow can easily be wiped out from maintenance on these older properties. 

You could list them all and 1031 the ones that fit into the timeline easily.    

My figures have the one park paying off the note just barely. the new park will pay off easily the other note or both with ease. 

@Payman A.You can easily do a 1031 and buy into a Delaware statutory trust DST in a self storage syndication.

I mostly rent to college students so an area they can hang out would be great but also don’t want anything that they can easily break - like moveable patio furniture.I was thinking about more solidified updates like built-in wooden benches around the fence.

But even this isn't easily done as reasonable multifamily properties come to the market once in few years...

I am very interested in multi-generational houses or especially homes that are easily convertible to allow for a junior attached ADU per California's definition.I have searched through literally thousands of house plans and noticed that very few of them have this ability.Has anyone else attempted to do this? 

Advantages are you can generally afford one house more easily than a multi, easier to finance, generally more sought-after and whole categories of issues are non-existent (ie noise of upstairs neighbor complaints).

Half of them are wrong, and the other half are easily misinterpreted by the non-practitioner.

Chicago is EXTREMELY neighborhood and block specific, so the data can skew quite easily.