I don't necessarily want to condone permitted work, but you should be alright. Having run a PM and contracting company in Chicago for the last six years, I can confidently confirm that quite a few investors take the same route. Where you could run into some road blocks is if you're renting any of the units out as Section 8. Then you're having a trained eye inspect the units periodically. Even then, not the end of the world...they may just ask you to fix it and its generally not too comprehensive. Again, not condoning unpermitted work, but I've seen the worst of the worst in Chicago and it really only becomes an issue if something is visibly wrong and reported by a neighbor or angry tenant. At the end of the day, tenant safety and liability is the priority, and if that's not an issue, you should be fine. To your note about the tenant complaints, (usually) the only two times I see tenants get involved in those matters are if their quality of life is affected by a building malfunction or if they're what I would call "professional" tenants. There are plenty of people in Chicago who know how to leverage landlords, withhold rent until the issue is resolved, not pay rent for 6-8 months, and move onto the next place before they can be evicted. Chicago is extremely tenant friendly as I'm sure you know, which makes it impossible to evict tenants quickly through the city. You can avoid the first part by just being an attentive landlord to maintenance issues (whether it's you or a pm company), and the second part can usually be avoided by being diligent in the application process. I personally wouldn't have had the patience myself, but I had a client who owned 150 units, and even after hiring us, chose to do a 30 minute interview with every applicant prior to accepting them. With that being an extreme end of the spectrum, I would just recommend a lease history and landlord verification along with the background check.