Don’t just run your property—shape its future, one quarter at a time
Owning a multi-family building means being pulled in ten different directions every day—rent collection, maintenance, tenant communication, emergencies, upgrades, taxes… the list doesn’t end. It’s easy to stay stuck in the weeds, reacting to whatever’s loudest.
But the most effective property owners don’t just manage. They plan.
That’s why this time of year—right as one quarter ends and another begins—is the perfect opportunity to step back and look ahead. Not with a vague wish list, but with a practical framework to guide the next 12 months.
Gus Grimstad, a property manager and small business owner based in Wisconsin, is known for taking this kind of thoughtful, quarter-by-quarter approach. He doesn’t wait for problems to show up—he plans to avoid them. And more importantly, he builds time each season to move his property forward, not just keep it from falling behind.
Here’s how you can do the same.
1. Start With a “Property Health Snapshot”
Before making plans, you need to know where things currently stand.
Set aside a quiet hour to evaluate:
- Occupancy: Are all units filled? If not, how long have they been vacant?
- Tenant satisfaction: Any recent complaints, late payments, or signs of turnover?
- Maintenance backlog: What repairs are overdue or frequently delayed?
- Financials: Are you on track with income goals? Any unexpected costs?
- Upgrades: What’s aging or in need of attention this year?
This snapshot gives you a clear view of your building’s strengths and vulnerabilities—and lays the groundwork for smarter quarterly goals.
Gus Grimstad keeps a simple spreadsheet to track this review each quarter.
“It doesn’t have to be fancy,” he says. “But if you don’t know what’s working—and what’s breaking—you’re flying blind.”
2. Choose a Primary Focus for Each Quarter
Trying to tackle everything at once leads to burnout. Instead, choose one focus area per quarter. You can still handle day-to-day operations, but give special attention to one theme at a time.
Here’s a sample year broken down this way:
- Q1: Lease audits and renewal planning
- Q2: Exterior upgrades and landscaping
- Q3: Rent optimization and market review
- Q4: Financial cleanup, budgeting, and taxes
This rhythm keeps you focused while ensuring that every area of the property gets regular attention.
3. Build a Rolling Maintenance Plan
Most maintenance surprises… aren’t actually surprises.
Take what you’ve learned from last year and plot it into a seasonal maintenance calendar.
Example:
- January: Furnace checkups
- April: Gutter cleaning, landscaping begins
- July: HVAC inspections, window repairs
- October: Winter prep and snow contract review
Documenting this helps avoid emergencies, spreads out expenses, and shows tenants that you’re running a proactive operation.
4. Pre-Schedule Your Communication Touchpoints
If tenant communication has felt scattered or reactive, now’s your chance to systematize it.
Try this schedule:
- Monthly tenant updates (email or print): share maintenance reminders, building updates, or seasonal tips
- Mid-lease check-in: a friendly message halfway through each lease term
- Lease renewal letters: send 90 days in advance with clear options and incentives
Gus Grimstad emphasizes this point often:
“Consistent communication reduces complaints and surprises. It also builds trust—which leads to renewals.”
5. Revisit (and Raise) Rents With Strategy
Many landlords undercharge simply because they’re unsure of the market—or worried about losing good tenants.
Instead of blanket increases, take a strategic quarterly approach:
- Research local comps every 3 months
- Identify underpriced units
- Offer renewal incentives with modest increases
- Phase in adjustments gradually for long-term tenants
Raising rents doesn’t need to be aggressive to be effective. It just needs to be consistent and fair.
6. Strengthen Your Team and Vendors
A successful year isn’t just about the property—it’s about the people who help keep it running.
Each quarter, check in on:
- Your go-to vendors: plumber, HVAC, handyman, electrician
- Your backup list: do you have one?
- Your communication system: is it fast, reliable, and documented?
- Your property manager (if you have one): are they meeting expectations?
Quarterly check-ins ensure that your support system grows with your property—not against it.
7. Schedule Strategic Reviews (Not Just Emergencies)
Treat your property like a business. That means building in review and reflection sessions.
Try this cadence:
- Monthly review (30 min): What happened? What’s next? What’s off track?
- Quarterly planning (60–90 min): Deep dive into focus areas, financials, and new goals
- Annual reset (2–3 hours): Strategic vision, upgrades, growth plans, system upgrades
You can do this solo, or loop in your property manager or financial partner. The point is to run your rental like a real business—not a never-ending to-do list.
Gus Grimstad explains:
“Owners who stay in the game long-term aren’t chasing emergencies all year. They’re zooming out, reflecting, and making moves early.”
8. Plan for Breathing Room
Burnout is one of the top reasons landlords sell too early—or manage poorly. That’s why it’s critical to build margin into your year.
Plan for:
- Time off (and who’s covering for you)
- Slow months (and how to budget for them)
- Flex weeks (to catch up or get ahead)
You can’t control every surprise. But you can plan in a way that gives you room to respond without spiraling.
Final Thoughts: Run the Year—Don’t Let It Run You
If there’s one thing we can learn from people like Gus Grimstad, it’s that successful property ownership isn’t about chasing perfection. It’s about being intentional.
By approaching your year quarter by quarter—with a focus, a rhythm, and a sense of leadership—you create a smoother, saner version of rental ownership.
And that’s where long-term success lives.