In October 2025, I recorded a Q&A about the questions buyers ask most in Southwest Florida: hurricanes and insurance, HOAs, milestone inspections, rentals, old roofs and pipes, and appraisal gaps. Most of those answers still hold up a year later, and the insurance picture has improved. Below are my answers from the video, updated with dated 2026 facts. None of this is insurance or legal advice. For guidance on a specific policy, talk to a licensed insurance agent.
How do you keep a Southwest Florida home insurable?
Pick a house that insures well: a newer roof, full impact windows and doors, a house that sits higher and a documented wind-mitigation inspection. Together, those features lower the risk to the house and the premium.
For every address, we check the roof year, the impact rating, how high it sits and the flood zone. If a property sits low and lacks impact features, we budget for upgrades with a seller credit or move on to a home that fits better.
What’s new since the October 2025 video:
- Insurers must offer discounts for wind-resistant features such as roof-deck attachment, roof-to-wall connections, opening protection and secondary water resistance (s. 627.0629). The inspection uses form OIR-B1-1802, and the revised Rev. 04/26 version has been required since April 1, 2026. A report remains valid for up to five years if the home has no material changes (Florida OIR).
- Since 2022, an insurer can’t refuse to write a home solely because its roof is less than 15 years old. An older roof can still qualify with an inspection showing at least five years of remaining life (SB 2-D).
- My Safe Florida Home still offers grants of up to $10,000, but the home must be homesteaded, built before 2008 and insured for $700,000 or less. Since SB 1452 took effect on June 26, 2026, grants have been limited to low- and moderate-income applicants. A second home doesn’t qualify.
- The 2026-27 state budget created a sales-tax refund of up to $500 per home for impact windows and doors purchased from July 1, 2026, through June 30, 2029 (Governor’s office).
Are insurance costs still out of control?
Florida is still on the high side, but the direction has changed. In the October 2025 video, I said the same house can price very differently across carriers depending on roof age, electrical and plumbing updates, and the deductible you choose. That’s still true. The market around it has moved:
- Citizens, the state-backed insurer, cut its average homeowners multiperil rate by 8.8% for 2026. Every personal-lines policy dropped by at least 2%.
- Citizens had 254,918 policies in force on September 25, 2026, down from about 1.41 million at its October 2023 peak (Citizens).
- As of May 2026, the state regulator counted 20 new property insurers entering Florida since the reforms. In September 2026, the regulator said filings over the prior 30 days averaged a 4.8% requested decrease.
Second-home owners should watch two rules. Citizens’ glide path caps annual increases at 15% for a primary residence, but a second home can increase by as much as 50% a year. And once a private insurer offers comparable coverage within 20% of the Citizens premium, you can’t renew with Citizens (SB 2-A analysis).
In the video, I mentioned taking over a seller’s more favorable policy. Flood insurance is the policy that clearly transfers, as explained below. A homeowners policy is the seller’s contract, so ask the carrier before counting on it.
What changed for flood insurance?
Two dates matter. The federal flood program is authorized through December 11, 2026, and Citizens’ flood requirement reaches every homeowners policy with wind coverage on January 1, 2027. Condo unit policies are exempt. A 2026 bill that would have widened the exemptions died in committee.
The basics haven’t changed. Standard homeowners policies exclude flood. Flood insurance is required for federally backed or federally regulated mortgages on buildings in high-risk A and V zones, and FEMA says about 1 in 3 flood claims come from lower-risk zones. A new NFIP policy has a 30-day wait unless it’s purchased with the mortgage. Under Risk Rating 2.0, most existing policies can’t increase by more than 18% a year.
The October 2025 video came out during the fall shutdown, when the program lapsed from October 1 to November 12, 2025 and new policies couldn’t be written. Even during a lapse, a seller’s existing policy can be assigned to the buyer. Under Risk Rating 2.0, the buyer keeps its discount path (FEMA FAQ).
Before you commit, check:
- The flood zone. Lee County and Cape Coral have online lookups, while Collier’s floodplain office has a map and hotline. Six panels in unincorporated Lee change on March 2, 2027.
- Any elevation certificate on file for the property.
- The seller’s flood disclosure. Since October 1, 2025, sellers must disclose known flood damage, flood claims and federal flood aid under s. 689.302.
- A real flood quote for the address.
How do you avoid HOA and special-assessment surprises?
Surprises are scary. Documents aren’t.
Before you commit, we get the budget and the reserve figures, the engineering and milestone reports, and the recent board minutes. If the reserves are underfunded or there’s a big project with no plan, we factor that in before you’re locked in. You can still make an offer. This review happens during the inspection and due-diligence period.
Condo rules have become firmer since the October 2025 video. The December 31, 2025, deadline for structural integrity reserve studies has passed, reserves for those items can’t be waived, and resale buyers have 7 days to cancel after receiving the documents, not counting weekends and legal holidays. Jarrett’s condo rules post has the full list.
For a home in an HOA, the seller must deliver a disclosure summary before you sign. If it isn’t provided, you can cancel within 3 days of receiving it, but not after closing (s. 720.401).
An update since the October 2025 video: the law no longer ties milestone inspections to how close a building is to the coast. That automatic coastal trigger was removed in 2023. Condo and co-op buildings with three or more habitable stories need an inspection at 30 years, and the local building official may require it at 25 years near salt water (s. 553.899).
Should you wait for prices to drop?
In October 2025, I said the market was balanced. Waiting might save a little, but it could also cost you the house or location you want. I expected the market to tip toward sellers within 12 months as rates fell and the property-tax vote approached.
Inventory did tighten. NABOR reported 5.4 months of supply in August 2026, down from 8.1 a year earlier, while active listings fell 16.3%. Prices didn’t jump, though. The median closed price was $575,000, down 1.7% (NABOR, September 25, 2026).
I also said the vote would eliminate property tax for full-time residents. That isn’t what’s on the ballot. Amendment 3 would increase the homestead exemption on non-school taxes to as much as $150,000 in 2027 and $250,000 in 2028 for people who were permanent residents by December 31, 2026. It needs 60% approval on November 3, 2026. Jarrett’s 2026 changes post has the details.
Will a property rent in season?
If the property matches seasonal demand, yes. First, we check city and county rules, then the HOA documents. Some gated communities allow only a few rentals each year and require 30 days between them. Some condos allow weekly rentals.
Florida law generally bars local governments from banning vacation rentals or limiting their length or frequency unless the rule dates to June 1, 2011 or earlier (s. 509.032). HOA and condo documents can still restrict rentals, so they’re usually what decides the issue. Stays of six months or less also carry a 5% tourist development tax in Lee and Collier, on top of sales tax. On November 3, 2026, Collier voters will decide whether to increase that tax to 6% starting January 1, 2027 (Gulf Shore Business).
Are an old roof or old pipes deal breakers?
No. But they have to be handled. The cost of replacing an older roof either needs to fit your budget or become part of the negotiation. Sometimes homeowners insurance isn’t available until the work is done, so the seller replaces the roof before closing.
Polybutylene piping turns up in some older condos. It needs to be replaced, and it’s costly. We’ve negotiated roof and pipe repairs before closing. Finding them during the inspection period is what matters.
What if the appraisal comes in low?
Everything is negotiable. A seller’s asking price doesn’t determine what the house is worth, and the bank sees it the same way. When you love a property, we prepare a packet of comparable sales for the appraiser.
In some communities, one floor plan can have 10 to 15 variations based on features and upgrades, lot location and sun exposure. A bare-bones version isn’t a fair comparison for a fully upgraded one. If the appraisal still comes in short, we can challenge it. A second appraisal is also an option.
If you’re comparing homes in Naples, Fort Myers or Cape Coral, send me the addresses. I’ll pull the roof year, flood zone, insurance picture and HOA documents for each. You can browse homes or reach me here.
