We will follow a family that decided to rent out a home as a side job before retirement. They planned to create a steady income each month by renting out their home instead of selling it. Since this was their first time, they organized the steps and tackled them one by one.

First, they set the rental price. According to Zumper, the average rent in Madison for June 2026 is $1,675, which is $275 lower than the national average. There has been no change in the past month, and it has decreased by 1 percent compared to a year ago. This family did not use this average directly; instead, they selected a few similar listings in the same neighborhood with the same number of bedrooms to compare and determine the final amount.

To determine the exact amount, they compared four to five listings with the same number of bedrooms in the same neighborhood in a table. The online average can be a broad number that may differ from the actual neighborhood market rate. They also considered that setting the rent too high could lead to longer vacancies, which could result in greater losses than simply lowering the rent a bit.

After setting the rent, they posted an advertisement. They uploaded photos and descriptions on both Zumper and Zillow Rental Manager, clearly stating the rent, security deposit, and pet policy. By disclosing the conditions upfront, they reduced inquiries that would have been a waste of time.

Once inquiries started coming in, they began the tenant screening process. They checked the credit score, income verification, and previous rental history in that order. They used the criterion that income should be at least three times the rent and called the previous landlord to ask if there had been any late rent payments. Only after going through this step did they select one tenant they liked.

When receiving applications, they requested a copy of a government-issued ID, recent pay stubs for the last two months, and the previous landlord's contact information. Having these documents made the decision-making process much clearer.

The next step was drafting the lease agreement. They documented the rent, payment date, security deposit amount, contract duration, maintenance responsibilities, and pet policies in writing. Since they planned for regular income after retirement, they also included an automatic rent payment clause in the contract.

Signing the lease did not mean the family's role was over. In Wisconsin, landlords are obligated to maintain basic facilities like heating, plumbing, and electricity in proper working order. They created a move-in condition checklist and recorded every corner of the house with the tenant, which helped avoid disputes during the security deposit settlement later on.

Regarding the security deposit, Wisconsin has no maximum limit. However, it must be returned within 21 days after the tenant vacates, along with a statement of deductions. If this deadline is missed, the full deposit must be returned, and the court may impose double the unjust deductions and legal fees.

They also prepared for situations where rent might be late. In Wisconsin, a five-day notice for payment or eviction must be sent first. If the overdue amount is paid within this period, the contract remains intact.

By following these steps, they successfully completed their first rental agreement without major issues.

If you are moving from another state to Wisconsin like this family, keep in mind that property taxes and winter heating costs may differ from your previous state. It is more realistic to calculate the actual amount left after considering property taxes, insurance, and maintenance costs, rather than judging solely based on rental income. When approaching as an investment, do not assume that market prices will continue to rise; it is wise to consider variables like vacancies and repair costs as well. Madison, being a college town, tends to see a surge in inquiries at the beginning of the semester, so timing your advertisement before the semester starts can help reduce vacancy periods.

However, since taxes and contract details can vary by situation, the information provided here should be considered general advice, and it is recommended to consult with a lawyer or real estate professional before finalizing any contracts.