Bay Area homeowners spending $5,000–$30,000 on an outdoor project have one thing in common: most of them wish they'd asked more questions before starting. The questions below won't cover every situation, but they'll tell you a lot about who you're dealing with — and whether you're set up for a smooth project or a difficult one.
Most Bay Area outdoor projects above a certain height or scope require a permit. Fences over 6 feet, most gates, and any deck or patio construction almost always need one. Before any work starts, you need to know: (1) is a permit required, (2) who is applying for it, and (3) what happens if the build doesn't pass inspection. If the person you're hiring says 'we don't worry about permits' — that's a red flag. You're the property owner. You're the one who faces fines.
A low bid often reflects a narrow scope. Common exclusions that show up as surprise line-items later: demo of existing fence or structure, stump or root removal, grading or slope work, permit fees, gate hardware, concrete footings, and delivery surcharges for hillside access. Get an itemized proposal and ask specifically: 'What would cause this price to change?' A good project manager tells you upfront. A contractor who can't answer this question will be harder to deal with mid-project.
Some contractors build with their own licensed crew. Others subcontract the labor to whoever is available that week. That's not inherently bad, but you should know. If something goes wrong — and things do go wrong — you need to know who is accountable. Is it the person you hired? Or a sub they brought in who has no direct relationship with you? This is the core reason some homeowners choose a project management company instead: accountability stays in one place, regardless of who performs the build.
Bay Area projects regularly run late due to permit delays, material lead times, crew scheduling, and weather. This is normal — but you should understand the realistic schedule before committing. Ask: when does work start, what is the sequence, how long is each phase, what are the dependencies, and what causes delays? A contractor who can walk you through this has done it enough times to know. One who quotes a vague '2–3 weeks' without specifics probably hasn't thought it through.
It will. A board gets damaged. A post shifts in the rain. The gate doesn't swing level. The question isn't whether issues arise — it's who handles them and how fast. Before signing anything, ask: what is the process for punch list items after the build is complete? Do you offer a warranty, and what does it cover? How do I reach you if something needs to be corrected? The answer tells you a lot about how seriously they take the relationship after the check clears.
Our answers to all five of these questions are in our first call.
We handle permits, own the scope, manage the contractor, walk you through the timeline, and stay in the relationship after the project closes. That's the model we built around the questions homeowners always wish they'd asked.
Start Your Project© 2026 Redwood Outdoor Co. All rights reserved.
← All Articles