Your problem is likely in the data you relied on for your expected return and their experience.

I've been managing places for my aunt up here and in SoCal for about a year now and personally believe that how often a tenant asks for fixes is more based around their personality than anything else.Take my opinion with a grain of salt as I've never used a PM service so don't have any data to actually compare.

Explaining the reason for the increase and providing some market data to show how rental prices in the area have risen could make things clearer for the tenant.

Hi Matthew,This data is a macro look at median sales price of all property types within those four cities limits.

I only have 7 months of data, but other hosts say Padsplit tries to at least keep everyone as close to 80% as possible. 

If you want this to be a real business, test out pricing levels to see what the market will bear.

When you surround yourself with a great team, are well-educated, and use data to make your decisions, your odds of a significant issue are VERY LOW.Continue to network with the awesome community here in Chicago, and you will stay on the right path.

That said, it can be done and done successfully if you plan in advance, build your team (contractors, subs, back ups, lenders, credit with suppliers, escrow/title, real estate attorney, mentor, etc.) get educated on finding (marketing) for deals, rehab costs, locations, market data (like crime rates, school ratings, population growth, job growth, etc), specific market insights like what is most popular and sells for the most in your area, etc

If it is schedule showings and transmit financial data and proffer the MLS commercial form contract then probably not.

Gather data on comparable properties, their rental rates, and occupancy levels to present to lenders.