I haven't seen a program that does every single thing well.

Once you have a shortlist, sign up for an account with each one and test them extensively to see how they function.

@Jay RitchieI came across this website which I think could help you: https://www.leadsafechicago.or...If you qualify for the city's programs, you may be able to get it done for free or at a discount.

@Miranda LeMaster If your agent can not offer you a good commercial option, then you are working with a personal lines agent and you may want to think about making a change sooner than later.Ideally you want to have 2 separate insurance programs.  1 for your personal and 1 for you business/commercial exposures.  

In my experience the basics for a functional RE based CRM are:Custom Fields for Data Objects (Leads, Prospects, Applications, Buildings, Units, etc...)A Screening Engine (background/credit checks, employment verification, etc)Online Rental Application (this should automatically run the application through screening)Ability to mass email/sms leads and tenants to provide informationSurveys/Inspection formsI've been building real estate CRM tools for years.

Assuming the schedule holds, we'll have some people from Section 8 Housing coming to share about the program and provide us with some time to ask questions.

I also know Breezeway has a program for $49/per month per property that do 24/7 guest assist 

His program sounds great!

I've used other programs for it in the past, but I like that Baselane is both a banking and bookkeeping platform built specifically for real estate investors.

There is a huge variance in underwriting guidelines, programs, rates, etc.Send me a message if you want to dive in to the scenario any more!