This is a task to handle carefully and at arms length. 

Most of her Chicago landlords do not charge a deposit since the anti-landlord penalties can result in paying triple back to your former tenant for some minor infraction.

... our friend here is only having operating partner in different project, that's hell of difficult task to do because you can't control your partner if they're not under your payroll.

Is it advantageous, or is it difficult and anti-foreigner with extra stamp duty and such?

If a landlord needs to enter a property for an inspection or repair, a two-day notice is required.Our Governor passed anti-squatting legislation a few months ago which allows owners to have the police remove them as opposed to before where it was considered a legal issue for attorney's to deal with.

I haven't done a 1031 exchange, but may in the near future and the small amount of research I have done on it seems to indicate that some qualified intermediaries only do the intermediary task (hold your money while you close on the new deal) and some try to do other tasks as well, like facilitate you finding the next deal, etc. 

This type of partnership will likely include managing partners and acquisition managers tasked with finding and structuring the deal.

However, in the case of safe unpermitted units there is a state sponsored agency (HCD) that is tasked with getting jurisdictions to comply with the various laws regarding providing housing units.  

There are rental management tools like Stessa, Baselane, Innago, and many others that include income/expense tracking that handles all the accounting tasks and reporting you really need for rentals. 

@Jaren Woeppel , after looking at the available local options, we continue to self-manage although we export a number of tasks, ie. answering the phone.