Additionally, make sure the deal itself is strong.Best regards, Stevan

If someone wants to host MTR, STR, whatever, they should start their own management company, not try to use this model where they can make additional money off of an owner if a property performs well.

. $150 plus tax Clean up fee at check out and $22 plus tax per day resort feePRIVATE OWNERS: $100 per day resort fee up to 2 people, $50 each additional person.

Therefore it's quite normal for a design change to be an additional service fee. 

Additionally the suburbs have higher taxes compared to Chicago proper.  

Is it to build up assets, is it to make additional income, is it to reduce your monthly housing spend and save more money, is it tax breaks/benefits? 

Keep the deposit towards additional rent if allowed by law and wish them the best of luck solving their problems. 

If the building is currently recognized as a single family residence,  then you are changing use and presumably will need to sprinkler the building and satisfy other fire rating and STC rating requirements not to mention the added costs of having to run mechanicals for multiple units, multiple kitchens, additional bathrooms etc.  

If you have any additional tips or resources on setting this up or ways to avoid the common pitfalls in this field, I’d be grateful to hear them.Thank you for offering to share a step-by-step blueprint—it’s exactly the kind of actionable guidance I’m looking for to make sure I approach wholesaling the right way!

I always ask within 24 hours of check-in to see if everything is okay-- but I think it takes people time to move in and see if anything additional is needed.