For most Florida associations, a roof replacement is the largest single contract the board will ever approve. It is also where the gap between the board and the contractor is widest: the contractor does this every day, and most board members do it once.
Our founder learned this firsthand as Vice President and Treasurer of a 132-unit Tampa HOA during a roof and gutter replacement project spanning 33 buildings.
That board missed the warning signs for five years. During that time, it continued budgeting for roof repairs rather than commissioning an independent assessment of the roofs’ remaining useful life and condition. That decision ultimately turned into a crisis when all of the roofs began leaking across the community.
What could have been a planned and manageable replacement project instead became an urgent, high-stakes undertaking. With limited time and fewer options, the HOA was placed in a much more vulnerable negotiating and financial position — and it paid the price for that delay.
The lesson is simple: when a major capital asset is approaching the end of its useful life, deferring an independent assessment rarely eliminates the problem. It usually eliminates your options. If you’re not sure how close your roofs are to that point, the free Property Risk Pulse scores your roof and reserve exposure in about four minutes.
1. Who defined the scope, and do they profit from it?
If the contractor bidding the job also decided what needs to be replaced, the board is relying on the seller to tell it how much to buy. That isn’t necessarily dishonest, but it is a conflict of interest.
What to ask for: an independent condition assessment that identifies what actually needs replacing, what can be repaired, and what can wait. Use it to write a single scope that every bidder prices. An Essential Scan gives the board that independent starting point before the first bid arrives.
2. Are the bids actually comparable?
Three bids are only useful if they describe the same work. Differences in underlayment, flashing, ventilation, gutters, disposal, and allowances for deck replacement can make a low bid the most expensive one by the end of the job.
What to ask for: a bid form based on your scope, with line items for each component and a unit price for rotted decking or other hidden conditions.
3. Is the contractor properly licensed and insured?
In Florida, roofing work requires a state-licensed contractor. Verify the license yourself at myfloridalicense.com rather than relying on a copy of a card.
What to ask for: certificates of insurance for general liability and workers’ compensation, naming the association as certificate holder, sent directly from the insurance agent. Confirm the coverage limits are appropriate for a project of this size.
4. How are payments tied to verified progress?
A payment schedule that front-loads the money removes the board’s leverage. Florida law places conditions on contractors who take large deposits, but the board’s best protection is a schedule that pays for work that has been completed and verified.
What to ask for: payments tied to defined milestones, such as buildings completed and inspections passed, with a retainage held until final completion and closeout. Someone who does not work for the contractor should confirm each milestone before the board pays it.
5. How will the association be protected from liens?
Under Florida’s Construction Lien Law, subcontractors and suppliers who aren’t paid can place a lien on the property, even if the association paid the general contractor in full.
The contractor’s lien rights are essential to understand. You are on the clock the moment the contractor considers the project complete.
What to ask for: a list of every subcontractor and supplier, copies of any Notices to Owner the association receives, lien waivers with each payment, and a final contractor’s affidavit before the final payment is released. Receiving this waiver is the key to a good night sleep after the project has been completed.
6. What do the warranties actually cover?
There are usually two warranties: the manufacturer’s warranty on materials and the contractor’s warranty on workmanship. They cover different failures, last different lengths of time, and often require registration or specific installation practices to be valid.
What to ask for: copies of both warranties before signing, confirmation of who registers the manufacturer’s warranty, and written confirmation that the installation will meet the manufacturer’s requirements.
7. What fees are being charged, and to whom?
On large projects, the contractor’s price is not always the only cost. Property management companies, consultants, and project managers may charge fees tied to the project, and those fees aren’t always visible to the board in the contract it votes on.
On that 33-building project, undisclosed project management fees from a third-party eventually became the subject of a legal dispute. That experience is why we now tell every board: ask in writing for every fee that any party will earn from this project, and get the answer before the vote.
8. Who will verify the work before the board pays?
The contractor’s progress report tells you what the contractor says was done. The building inspector confirms that the work meets code. Neither tells the board whether it got the scope, materials, and quality it paid for.
What to ask for: an independent verification process, with documented inspections at each milestone and a final walkthrough against the original scope before retainage is released. This is what the contractor oversight module in Portfolio Oversight is built for.
Before the vote: a one-page summary for owners
Owners will eventually ask why the board chose this contractor at this price. A short written summary, covering the independent scope, the bids received, why the winning bid was chosen, and how the board will verify the work, protects the directors and builds trust with the community.
This article is general information, not legal advice. Confirm contract terms and lien protections with your association attorney before signing.
Sources: Florida Statutes Chapter 713, Part I (Construction Lien Law) and §489.126 (moneys received by contractors); license verification at myfloridalicense.com.