The property has a few broken windows with boards up over them, an interior door off the hinges, rot on the bottom of the cabinet under the kitchen sink from a leak some time ago, water seeping up from the concrete in a back room making the carpet damp if it rains a lot.

@Juan Alberto Perez - FloresThe property had lots of water damage.

You're putting down 20%.Water/sewer looks high.

In Milwaukee, most often, tenants pay all utilities except water however, many pay water too.

My Question; is it legal for me (property owner/landlord) to create a signed agreement with future Tenants that states, when the outside temperature drops below a certain degree they must "trickle" water from all faucets to prevent bursting and frozen pipes?

If you need to put in a hot water heater or something, reach out and I'd be happy to help.On another note, I wish we had a Cumming meet-up.

Our insurance company wanted us to replace both water heaters before insuring our home but ultimately okayed it based on that they both had drains and we already had a warranty transferring on the home.

If its not either one of those I'd fo a water test on the plumbing waste. 

Generally tenants pay all utilities, but its very common for landlord to pay water around me.

Examples: I take a refundable pet deposit instead of a non-refundable one or a monthly fee, I currently pay the whole water bill without taking money from tenants because the duplex is watered together (I will eventually get a separate meter but the outlay is more than I want to pay right now) assuming it doesn't get out of control, paid for the new doorknobs on the bedrooms because the tenants requested locks despite the lead tenant saying they would pay for it, planning to replace the microwave hood simply because it's louder than it should be though it still works, etc.I'm probably losing out on a minimum of $100 monthly.