Hurricane season begins June 1 and runs through November 30 — but the preparation window closes well before that. Contractors fill up in May. Generator parts ship with 2–3 week lead times. Tree trimming crews that could have come in April are unavailable by late May. The annual pre-season inspection for Florida property managers should be done in April or early May, not the week before a named storm appears in the Gulf.
This checklist covers the ten inspection and preparation items that matter most for Florida property managers. Each item is followed by what specifically to look for, document, or arrange.
1. Roof Condition — Document With Photos
Annual roof inspection and photography is the single most important documentation practice for property managers in Florida. Before hurricane season, inspect the roof and capture dated photographs of:
- All four roof elevations from ground level
- Roof surface close-ups showing shingle condition, ridge cap, flashing, and vents
- Any existing damage, repairs, or areas of concern
If inspection reveals damaged shingles, lifted flashings, or areas of concern, address them before hurricane season — a roof with pre-existing damage going into a storm will face coverage arguments about pre-existing condition. Document all pre-season repairs with dated invoices.
2. Gutters and Drainage
Clogged gutters cause water to pool against the fascia and potentially infiltrate the roof edge — a common source of interior water damage that insurers sometimes attribute to maintenance failure rather than storm damage. Before hurricane season:
- Clean gutters and downspouts
- Confirm downspouts direct water away from the foundation
- Check for and repair any gutter sections that have pulled away from the fascia
- Confirm drainage around the structure is directing water away, not pooling at the foundation
3. Windows and Doors — Impact vs. Shutters
Florida building codes in most counties now require impact-rated windows and doors for new construction and major renovations. For existing properties, determine what you have:
- Impact-rated windows and doors: Inspect for any cracked or compromised glass, damaged frames, or failed seals
- Hurricane shutters (accordion, panel, or roll-down): Test full deployment and retraction of every shutter; check hardware for corrosion and ensure all panels are present and stored
- Plywood boarding plan: If neither impact glass nor shutters exist, have a documented plywood boarding plan with materials pre-staged or sourced
4. Generator and Fuel
If your property has a standby or portable generator, annual pre-season testing is essential — generators that sit unused for months can fail to start when needed.
- Run the generator under load for at least 30 minutes
- Check oil, coolant, and fuel levels; change oil if due
- Test automatic transfer switch (if applicable)
- Confirm fuel storage capacity and rotation plan (stabilized fuel or propane)
- Verify generator capacity covers critical loads (refrigerators, HVAC, sump pumps)
5. Tree Trimming — Within 10 Feet of Structure
Branches overhanging or within 10 feet of the structure should be trimmed annually. Beyond trimming, assess the structural health of mature trees near structures. Dead limbs, split leaders, and stress cracks in major branches all create storm damage risk independent of branch proximity. Hire a certified arborist for mature trees — not just a tree trimming service.
When a neighbor's or your own tree causes damage during a storm, the question of whether it was in good health and properly maintained becomes part of the claims and potentially litigation record. Dated photos showing trimmed trees and invoices from licensed arborists create a documentation trail that establishes reasonable maintenance — relevant both for your claim and for any liability dispute with a neighbor.
6. Outdoor Furniture and Loose Items Storage Plan
Outdoor furniture, grills, planters, signage, and other loose items become projectiles in hurricane winds. Before hurricane season, identify every loose item at each property and document your storage plan:
- Where will each item be stored when a storm approaches (garage, storage unit, inside the structure)?
- Who is responsible for executing the storage (management, tenants, specific vendor)?
- What items cannot be stored and require alternative protection (large planters, permanent outdoor equipment)?
7. Emergency Supply Kit
Property management offices and properties with on-site managers should maintain an emergency supply kit. Minimum contents:
- Battery-powered or hand-crank weather radio
- Flashlights and extra batteries (or hand-crank)
- First aid kit
- Waterproof bag with copies of insurance policies, property documents, and emergency contacts
- 7-day supply of water (1 gallon/person/day) if on-site staff may shelter in place
- Tarp and basic tools for emergency protective repairs
8. Tenant Emergency Contact Update
Send a pre-season letter or email to all tenants in May requesting confirmation of current contact information: primary phone, secondary phone, email, emergency contact outside the household, and planned evacuation destination. Also distribute your property management emergency contact information and the property's hurricane procedures (when to evacuate, what to do with outdoor items, how to reach maintenance in an emergency).
9. Insurance Policy Review
Annual insurance review before hurricane season should confirm:
- Coverage limits relative to current replacement costs
- Hurricane deductible amount and percentage calculation
- All policy endorsements — compare to prior year for any new restrictions
- Flood insurance status and current coverage limits
- Loss of rents sublimit adequacy
- All properties confirmed on the policy with current insured values
10. Vendor Contract Renewal
Pre-storm vendor agreements are significantly more favorable than post-storm emergency rates. Before hurricane season, confirm or renew agreements with:
- Roofing contractor (preferred vendor agreement or at minimum a confirmed relationship)
- Water extraction and mitigation company
- Board-up and emergency tarping service
- Tree removal and debris service
- Generator service company
The pre-season checklist is easy to deprioritize until the calendar says June and a system is forming in the Caribbean. Set a recurring April 1 calendar reminder titled "Hurricane Season Prep — Start Checklist" and treat it like a property tax payment: non-negotiable, same time every year, early enough to act before the deadline matters.
Run your pre-season checklist in LossHQ
Track inspection status across your entire portfolio — roof photos, vendor confirmations, insurance review completion — property by property.
Start Free — No Card Required →The Bottom Line
The annual pre-hurricane season inspection is the lowest-cost, highest-return activity in Florida property management. Every item on this list either reduces the probability of damage, reduces the severity of damage when it occurs, or strengthens your documentation for the insurance claim that follows. Complete it in April or May. Document everything. And for the documentation side of preparation, see the Florida insurance claim documentation kit.