I have clients doing 1 a quarter thats about the slowest to others that will go on a mini tear and I will help them buy 5 or 6 over a 45 day period then they go to work.But generally my busy folks will do 15 to 30 plus a year..

At some point long past a previous owner had converted a bedroom to a bathroom in this apartment.

Typically, a buyer going directly to the listing agent just doubles the commission that listing agent receives, will little or no savings to the buyer (or seller).6.

Still, we've re-opened our VRBO listing and have just started a listing with Mini Stays to see how they perform. 

Build sleeping pods that are mostly soundproof (double walled construction) and ventilated. 

DSCR loans are not that low and regular hard money loans will be in the double digits.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

This is a double-edged sword. 

. $50 per bedroom, so a 4-bedroom house will cost you about $150~200consumables - bathroom supplies, kitchen supplies, beverage supplies: $20~30 per week, depending on how much you providewear and tear - towels, linen, kitchen utensils, some furniture: $1000~2000 per yearRepairs/replacement for things that guests break or steal:  $1000~2000 per yearAlso, if your personal use is less than 14 days a year, the entire property's expense is deductible against STR income, but if you use more than 14 days, then you will have to calculate the proportion of how many days it's rented out vs how many days you or your family uses. 

Double check your lease, all the legalities and still check with the landlord....