Regardless of relative or not have all new occupants run through your application process. 

Daily or weekly I look at rent collected vs scheduled, past due balance, open maintenance tickets by age, turns in progress, and upcoming move outs for the next 30 to 60 days.

While making sure it cash flows when you move out and perhaps repeat the strategy.In regards to where; identify the path of progress, upper ranking school districts, new employment, population growth and median income growth.

What a fun journey but you are doing it and making progress

In Chicago, that rule is not applicable more often than people admit.I own and manage multifamily here, and I’ve watched otherwise “good” buildings quietly underperform once you factor in:Property taxes rising faster than rentsA real CapEx cycle approaching (roof, tuckpointing, boilers)Management intensity that no longer matches the returnEquity growing while cash flow stays flatI’ll add this because it’s relevant: I’ve personally sold a Chicago 4 unit building  in Rogers Park that was cash flowing.Not because it was a bad property—but because once I ran the keep vs sell math, the return on equity no longer justified the management, upcoming CapEx, and risk compared to other options.On paper, the building worked.

With that in mind, how are the following issues handled in practice:When plumbing, HVAC, or other building systems require service, does the tenant independently select licensed and insured vendors and obtain all required permits where applicable?

Hard to tell in an application/ screening who is going to be a busy body... 

Maintenance requests and work orders are centralized in the system, and a lot of the scheduling and follow-up can be handled remotely, with local vendors doing the actual work.Showings are mostly automated using self-showing/scheduling tools, while move-ins and move-outs still rely on someone local to verify the condition.We’ve used remote team members for admin-heavy tasks like maintenance coordination, application processing, and tenant communication.

We don't charge application fees and you may not want to either if you think you want to be pickier than normal with your tenants living right above you.  

Add to that a progressive income tax framework that steps down as the state hits defined financial benchmarks — with a clear path toward zero over time — and the long-term math starts to look very different for operators and investors.Layer in financing conditions, too.