Are you thinking about buying your first rental property? Being a landlord can be a challenging experience. There are many things to keep track of, and one mistake can cost you.
In our latest post, we have put together a checklist for the process of buying a rental property, the process of screening your tenants, and a list on how to manage once you are officially a landlord!
Own Your First Rental in Milwaukee: A Checklist
When You’re Ready To Buy
- Have Your Finances In Order – Before you start shopping, pull your credit reports and fix any negative marks. A lender will want to see strong credit, sufficient income, and a manageable debt-to-income ratio. I’ve seen new investors get pre-approved for more than they should borrow — don’t fall into that trap. If you’re unsure what you can realistically afford, speak to a mortgage broker or financial advisor who understands investment property lending. You’ll also want to set aside 3–6 months of reserves in case of vacancies or repairs — a smart move that’s saved me more than once.
- Set Your Limits – What can you afford to spend? Don’t compromise here. Struggling to make your mortgage payments will take the joy out of owning a home.
- Research – Talk to investors, read as much as much as you can, study your market’s trends, and consider buying a course. The best investors never stop learning.
- Take Notes – As you tour properties, it’s easy for details to blur together. Create a simple comparison chart with key criteria like square footage, rent potential, recent upgrades, repair needs, and neighborhood comps. I personally include a “gut feeling” column — sometimes your instincts pick up on things the numbers don’t. You can also record voice memos or videos during walk-throughs (with permission). Later, this will help you avoid decision fatigue and make more objective comparisons.
- Hire Professionals to Help – Navigating your first rental purchase without guidance can lead to costly mistakes. I strongly recommend building a local team that includes a real estate agent familiar with investment properties, a home inspector, a landlord-tenant attorney, and a CPA. For example, during one of my first deals, a sharp-eyed inspector caught a major foundation issue that I would’ve missed — saving me tens of thousands. Having these experts in your corner isn’t just smart — it’s necessary for protecting your investment and complying with local laws.
- Buy Below Market Value – One of the best ways to build equity from day one is to buy a property for less than it’s worth. In Milwaukee, I’ve seen investors target homes in transition areas like Washington Park or parts of Layton Boulevard West, where values are still rising and competition isn’t overwhelming. Look for motivated sellers, estate sales, or distressed properties that need cosmetic updates — these often sell below market. But don’t just rely on list price — run your own comps, get a second opinion, and know when to walk away. Buying right is one of the few variables you can fully control in a rental deal.
- Calculate a Property’s ROI – To calculate ROI, the net profit of your investment is divided by the amount of money you have invested. The results are expressed as a percentage or ratio.
When You Are Screening Tenants:
- Advertise – – First impressions matter, especially in a competitive rental market like Milwaukee. Use high-quality photos taken in natural light, and highlight key features like off-street parking, in-unit laundry, or a fenced yard. I’ve seen vacant units get filled within a week simply because the listing looked sharp and included a short video walkthrough. Post your ad on sites like Zillow, Rent.com, Craigslist, and local Facebook groups. Just be sure your description is clear, honest, and Fair Housing compliant — never mention demographics, preferences, or language that could be interpreted as discriminatory.
- Provide Application Forms – If a prospective tenant likes the unit, don’t lose them to friction in your process. Have printed applications on hand during showings, or better yet, use an online system like RentPrep or Avail where they can apply immediately from their phone. I’ve found that good tenants appreciate a smooth, professional process — it shows you’re organized and serious. Be transparent about your screening criteria upfront (credit score minimum, income requirements, background check), so you avoid wasting time on unqualified applicants and reduce the chance of disputes later.
- Background Check – Running a background check on prospective tenants is crucial. There are many services that can assist with this.
- Credit Check – In addition, running a credit check will help make sure your tenant will be able to pay you!
- References – It’s tempting to breeze through this step, especially if everything else checks out, but don’t skip it. I once ignored a reference call because a tenant seemed perfect — only to find out later they had left major damage at their last rental. When calling prior landlords, ask specific questions: “Did they pay rent on time?” “Would you rent to them again?” “Did they leave the unit in good condition?” Cross-check timelines on applications to catch inconsistencies. And if something feels off, trust your gut — it’s usually right.
- Sign an Agreement – Your lease should be rock-solid, legally compliant, and easy for tenants to understand. This is not the place to cut corners. I always advise first-time landlords to have their lease reviewed by a local landlord-tenant attorney, especially since Milwaukee has specific laws regarding security deposits, late fees, and required notices. Also, include terms for maintenance responsibilities, renewal procedures, and how conflicts will be resolved. A vague or DIY lease can open the door to legal trouble — I’ve learned this the hard way.
- Conduct an Inspection – Before handing over the keys, walk through the property with your new tenant and document everything. Use a standard inspection form and take time-stamped photos or video of each room, noting any existing wear or damage. I always have the tenant sign off on the condition report — it’s saved me from security deposit disputes more than once. Be sure to leave a copy for them and keep one for your records. A good inspection protects you both and sets a clear standard for how the unit should be maintained and returned.
- Clean & Repair the Property – Any repairs noticed during the inspection should be made before the tenant moves into the home.
- Change Locks – This is a small but critical step. You have no idea how many copies of the keys are floating around from previous tenants, maintenance workers, or even neighbors. In Milwaukee, I make it a policy to rekey every unit between tenancies, no exceptions. Not only does this protect your tenants and property, but it also reduces your liability if something goes wrong. In fact, in some landlord insurance policies, failing to secure the unit properly could complicate a claim. You can handle this yourself with a rekey kit or hire a locksmith — either way, do it before handing over the keys.
- Final Steps – Collect deposits, rent, and provide keys.
After Your Tenants Have Moved In:
- Tenant File – Create a tenant file with all the pertinent information. Keep track of all tenant issues.
- Calendar – Organization is key to keeping your rental business running smoothly. Set reminders for lease expirations, annual inspections, filter replacements, rent increases, and property tax due dates. When I had just one rental, Google Calendar was enough. But as I added more, I switched to property management software that tracks everything from lease renewals to late fees automatically. Being disorganized not only hurts your cash flow — it can also expose you to legal issues if you miss deadlines or fail to perform required maintenance.
- Stay on Top of Things – Maintenance can make or break your experience as a landlord. I recommend scheduling seasonal inspections — especially for plumbing, HVAC, and roofs — to catch issues before they become emergencies. One winter, I ignored a minor furnace issue in a duplex and ended up with a full heating system failure during a cold snap. That cost me $3,800 and nearly a lawsuit. Preventive maintenance not only protects your investment but also keeps tenants happy and renewals high. If you’re managing more than a couple of units, consider using property management software to track service requests and schedule recurring tasks.
- Master Vendor List – You will inevitably have to pay repair costs and maintenance fees. Work with vendors you trust for maintenance, plumbing, AC repair, etc. Keep their contact info readily available.