It will be tough to find a turnkey cashflowing property but you can certainly keep low expenses if you are interested in quad and live in one of the units.

Also with regards to the case worker, is it ok to keep them up to date with the difficulties or are they generally biased to the section 8 tenant?

Chicago is a tough sell due to the extreme weather.

Tough bit of luck there.

I did STR in a duplex starting back in 2017 and managed for others in North Conway, Ive since converted to all long term tenants and happy i did so... unless your property has something unique or a "rare" amenity.... like, sleeps 30, I honestly would not waste any energy on it in the north Conway area. so saturated, and so much big money being invested in the hotels, its tough to match amenities vs cost, and I see travelers trending back towards the hotel style accommodations. granted, for the right price, I'd buy anything and figure out what the best use for it is. use airdna.co for decent data on # of Short term rentals in any particular market. can also identify opportunities. the point of my response.... be careful in STR in any area and always have a plan B. you can change a lot of things about a property, but your cant change your basis!

But I get it when you have that tenant dynamic IE limited income basically lowest earners in the country its a tough group to corral for many many reasons..

The WA state credit union wherehe wanted to establish himself with a checking/savings accountrefused to take him. 800 credit, federal worker, very reliable, butout of state ID.

We've had a tough time selling our stuff and has taken 3-6 months to do so.

Probably going to be tough to find something in St Elmo that checks those boxes. 

Good mixture of travelers for the hospital systems, university, state workers and employers like GM.