(as in the triplex example) and studio for presumably less, paying $535 for a "room" in a house suggests to me that either there is a severe housing shortage in your area, those "rents" are inflated (because of frequent vacancies/evictions, etc) or you will have some very challenging tenants to deal with here.       

Chicago area investors buying 2-flats - There’s no shortage of classic Chicago 2-flats for sale around the city’s many neighborhoods, and if you’re willing & able to buy and renovate in a rougher area I can see how the finances may work, but I’m having loads of trouble making the numbers work in more desirable areas.Are there any Chicago BP users buying 2-flats in areas like Wicker or Humboldt Park, Bucktown, the Milwaukee corridor up through Avondale, or West Town/Ukrainian Village?

over supply, in the mid 00's we actually had too many houses for the population now we have the exact opposite a housing shortage that is unlikey to end anytime soon. its pretty simple economics everyone wants a roof over thier head and most people only want to own a single property (yes investors often own multiple but they are still renting to the population at large not affecting aggregate supply). so unless there is major housing supply increase which given that most major metros are out of land to build is extermely unlikely the housing market should continue to be very strong.

There is a shortage of affordable housing in the city so if a person is a waiter or waitress or within the service industry then its hard for them to find a place to live on their own without room mates.

Let's face it - we are at the top of the market (likely) and it is still strong now - only because we have an inventory shortage still and pent up demand because our real estate market was closed down for 6 weeks - but once many of these loan deferments come into play, people get off their big employment checks, and we see the covid shutdown results, I think we could be looking at a down turn. 

That said, if you determine this is where you want to be if you build the management systems around that type of property my guess is there will be no shortage of opportunity where current owners "tried their best" --  definitely not for the faint of heart.My 2 cents.b

As it comes in place it somewhere it is accessible (for emergencies, case flow shortages, construction mistakes, etc). 

It is a hard racket right now; with the shortages of housing, too many buyers, and a all time high of real estate agents...it's tough. 

Building vs Renovating - considering the crazy market, building new could be cost-prohibitive due to inventory/material shortages. 

:)we're closing on 20 units in Lorain and need a handyman for minor repairs, We have a great guy Rick Phares but he is currently going through some health problems unfortunately So please share whoever you know is looking for workAlso me and my partner are here for the rest of the week if anyone wants to meet up somewhere for dinner and talk about real estateIn the current climate we are in, with the massive labor shortages, I'd imagine it'd be impossible for an out of state investor to find a reliable handyman to work for them directly.