From the Wyo Stays team. A working template — the gated version is fillable.
Running a rental well is a year-round rhythm. This one-page annual calendar puts every recurring task — financial, maintenance, pricing, and compliance — in front of you so nothing sneaks up.
Q1 (Jan–Mar)
- Assemble year-end tax packet; hand to CPA (see that resource)
- Issue 1099s to contractors paid $600+
- Review last year's performance; set this year's revenue plan
- Renew insurance / licenses as they come due
- Winter freeze watch; roof snow load
Q2 (Apr–Jun)
- De-winterize; AC and exterior service after snow
- Refresh listings and photos for summer
- Set peak-season pricing + minimums (Rodeo, summer)
- Q1 estimated taxes (if applicable)
- Deep-clean and refresh furnishings
Q3 (Jul–Sep)
- Execute peak-season pricing; watch pacing on Rodeo/summer
- Mid-year books and P&L review
- Prep for hunting-season demand
- Q2 estimated taxes (if applicable)
Q4 (Oct–Dec)
- Winterize before first hard freeze (critical)
- Plan winter mid-term strategy to fill the trough
- Confirm snow-removal vendor
- Year-end maintenance and reserve review
- Q3 estimated taxes; year-end tax prep begins
Ongoing (every month)
- Update books; review pricing; test detectors; monthly maintenance checks
→ Unlock the fillable annual calendar, or → get a free evaluation — we run this rhythm for the properties we manage.