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

I  tried several time to request application to get my money back but never got it. 

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.

The average job opening now receives 242 applications, nearly triple what it did in 2017.

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.

It’s not cheap for tenants to move, and most would rather renew with a reasonable increase than incur moving costs, application fees, deposits, and uncertainty.As far as timing, winter markets do require more thought around turnover risk, but with strong demand even in January, the fear of winter vacancy is often overstated.

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.

Congratulations on your progress and keep up the good work.Start by educating yourself on the market you're considering. - Unemployment rates, if new jobs are coming to the area, crime trend (use spot crime or the crime map in NewsBreak), median income trend, population trends, renters to owners ratio, hot zip codes, best school districts, path of progress and last but not lease price-to-rent ratios.