If you’re a REIN member (to get a nice discount) check Parker insurance as they have policies driven to rental properties with several features not provided by othersOr ....check SquareOne InsuranceCheersEdison 

@Aaron T.The self-directed IRA (while not quite as feature-rich as the Solo 401k) is definitely the way to go if you are not eligible for a Solo 401k.

I'm using Tellus too and the features I've been using for now are totally free, just like what @Grant Delmonte said. 

quicken home and business will get it done for you and keep you organized and has rental reporting features like cashflow reports and schedule-E end of year reports.

I never had an significant incident (again knock on wood) at that property (which had a visible security system,  other visible security features, etc) all the newer townhouses in the area are constantly seeing package thefts and car prowls.   

You can break properties out by type etc.They have tutorials for free and will do a demo to show you all the features.

Thanks Paul 👍 Why not come to one of the Chicago RE meetups that features lots of networking time? 

I like the search features: https://www.biggerpockets.com/searchAlerts can be really helpful too: http://www.biggerpockets.com/alerts

There are so many software AppFolio, Propertyware, Buildium, RentManager all have their unique features.

Do not "trust" your employee won't file unemployment when you eventually fire them either.