As a side note, feel free to throw suggestions and let me know its a dumb move to buy property as primary residence and pay 7.5% mortgages, sit out. :) I wont mind at all.

If the tenant complains (even if he feels everything was deducted correctly), he offers them 30% of the amount he deducted back.

Nick at ReventureConsulting.com has all this and lots more targeted data with his free youtube videos.

Feel free to text me - I have a lot of connections with property managers that have large inventory for rentals. 

Feel free to reach me through PM  

Living with parents in Chicago suburbs but moving to Lakeview East (North side Chicago) next month to get a feel for living in the city.

Feel free to reach out of you have any specific questions.

I have not done too many deals in your market, and I anticipate things are nuanced depending on the property type and condition and based on the personality of the owner....BUT it is common and customary in my world, which is usually retail/med office, for tenants to have at least some time of free rent during the buildout.We usually structure things as follows, and you can change the number of days around but this is traditionally what we at least shoot for when we have a tenant we are repping.- Lease commencement date is to be the 6/1/24 or when the landlord's work is complete. and we traditionally have penalties in place if the LL's work takes too long and pushes us past our initial timeline.- then we typically have "rent commencement" or when you start paying rent, to be the earlier of either 180 days following lease commencement or when you are open for business.  

Invasion of privacy and likely "creepy" for the residents to feel they are being watched. 

If it is a normal 70/30 leveraged property, you may end up subject to tax on 70% of your returns anyways - so cost benefit, is that 30% tax free portion worth the high tax rates paid and additional filing fees to get tax free treatment on the 30%?