Five documents and one question. If any of it is missing, keep looking.
6 questions, and you should be able to ask all of them without any awkwardness at all. A contractor who is uncomfortable with any of these has told you something more useful than the answer would have.
1. Can I see your certificate of insurance?
It should arrive without being asked, and it should name you — or your management company — as certificate holder. If work on your property injures someone and the contractor is uninsured, the exposure lands on you. This is the one question with real money behind it.
2. What exactly is in the scope, surface by surface?
Not «paint the exterior». Which elevations, which trim, which doors, whether the soffits and the shutters are in. Scope ambiguity is where change-order arguments come from at the end, and it costs nothing to resolve at the start.
3. What happens on day one?
If the answer is «we start painting», that is the answer. On a coastal exterior, prep is around 70% of the work: wash, dry completely, scrape, repair, spot-prime. A crew that starts spraying the first morning is painting over the problem.
4. What products, and why those?
On the Gulf Coast the answer should mention 100% acrylic, elastomeric on stucco where appropriate, and marine-grade primer on metal. The material cost difference between these and standard products is small; the lifespan difference is years.
5. How is the money staged?
A deposit and a balance on completion is normal. A demand for most of the money up front is not. Neither is cash only.
6. Who is actually on my property?
Ask whether it is their crew or a subcontractor, and who supervises. The answer matters most on the fourth day, when the person who agreed the scope with you is no longer the person holding the brush.
The best single signal is a written scope. A contractor who will put the surfaces, the products, the timeline and the crew size on paper before taking a deposit has already answered most of these.
And one you should not have to ask
Whether the estimate costs anything. It should not, and it should be a visit rather than a number over the phone — a price quoted blind is a guess about substrate and prep, which are the two things that decide what the job really costs.
That is how we work: see what we do, or ask for a free estimate and judge us against this list.
