Quote from @Jeff Roth: Hi Lina from Texas-Congratulations on your interest in investing in mid-term rentals and you are wondering how and where to get started.I get this question frequently from investors.Sometimes and investor is looking to keep their property cashflow positive as insurance and taxes have squeezed cashflow by turning units into mid-term or short-term rentals.First off, ideally, the property will cashflow as a long-term rental should something disrupt the mid-term rental model.You will also want to have the property be near where there would be a demand for mid-term rentals (hospitals, universities, research centers).Monthly rents for mid-term rentals are about 20% (+/-) higher than unfurnished similar long-term rentals.There are property managers that will manage mid-term rentals for you and I always advise my clients to use property managers to keep their investment as passive as possible and for compliance issues related to Fair Housing Laws and local regulations.To Your Success! 

I can see in that one pic that you could use a bit more artwork on the walls.

Those who just try to copy the price model and not the operational leg, yeah they don't last long. 

We have sold (tax free), kept as long term and/or short term rentals as well.

There's no way it takes that long to shovel the sidewalk on a building of that size.Shop around and I'm sure you'll find someone that does it for much cheaper.

But also, how long does it take in this case?

As long as the city considers your property a true SF, you shouldn't have any issues getting this permitted (in theory, yet to see how some municipalities will handle this law).

Asking about the SW suburbs specifically, in the land of long sidewalks and big actual parking lots. 

Last year, I purchased a SFH under market at 7.65% interest rate and did some rehab to up the value.

As long as it's livable, you'll find a buyer.