All units are 2x2 with a basement that can be utilized as an additional bedroom + a 1 car garage.

Any recommendations for a good software that will allow me to customize contracts?

Based on what I could see through the windows, there is some furniture in the house but I don't  think the utilities are turned on.

We are planning to roll out a custom built property management platform later this year for Premier Property clients.

This means around the 1st of the year there is a temporary boom of unqualified renters entering the market and to make matters worse the temperature normally drops tremendously which increases the danger of frozen pipes or high utility bills (choose one or the other) insurance agents tend to frown upon vacancies... 

Verdan, I get to Milwaukee area 4 to 5 times a year with work, I have a couple customers just north of you.

It worked out great and he paid almost my whole mortgage then we split the utilities. 

My chat messages to them are still unread (1.5 weeks after posting).I am about halfway finished with onboarding at HostAway and have had several hiccups, but I think it will work out in the end; their customer support seems to be on top of it.

I haven't even officially automated my messages (I use saved drafts and slightly customize each one) and it still only takes me a couple of minutes per booking unless there are random questions. 30 minutes is probably only the case if there's a maintenance issue during the booking. 

Their portion of the rent is $115 a month as well as utilities.