San Diego Outdoor Living Contractor Due Diligence Checklist (Free PDF – 2025)
Updated November 2025 – San Diego County
Planning a significant outdoor remodel in San Diego County and trying to hire the right landscape contractor? Before you sign anything, use this free 2025 Contractor Due Diligence Checklist to uncover the hidden risks that lead to delays, cost overruns, drainage failures, and unfinished projects.
This checklist is especially helpful if:
- You already have one contractor you like and want to confirm they’re a safe choice.
- You’re comparing two or three bids and want an apples-to-apples way to stack them.
- You’ve been burned by a bad contractor before and never want to repeat that experience.
TL;DR – Why This Checklist Matters
- Most expensive mistakes are made before the job starts – during contractor selection, not during construction.
- Drainage, utilities and subsurface work are where shortcuts hide and where failures show up months or years later.
- Financially unstable or underinsured contractors are more likely to stall projects, cut corners, or walk away when problems arise.
- This checklist gives you specific questions to ask and the documentation to require from every contractor you interview.
Download the 2025 Contractor Due Diligence Checklist
The checklist is a printable, fillable PDF you can use side-by-side for two or three contractors. It covers licensing, insurance, subsurface work, drainage, utilities, project management, schedule, financial health, warranties and more. Each row explains why it matters and leaves space for notes so you can see, at a glance, who is actually protecting your home and who is gambling with it.
You can use it whether you end up hiring INSTALL-IT-DIRECT or not. The goal is simple – help you avoid the mistakes we are called in to fix every year.
How To Use This Checklist With Any Contractor
To get the most value from the checklist, use it during your conversations with contractors, not afterwards.
- Print one copy for each contractor. Write the company name at the top so you can compare them later.
- Ask every question out loud. Do not skip rows. You are testing both their answers and their reactions.
- Require documentation, not just verbal promises. Licenses, insurance certificates, sample schedules and written policies are all fair to request.
- Mark “yes,” “no,” or “unclear” for each item. Use the notes column when something feels vague or incomplete.
- Compare your sheets. The safest contractor is usually the one with the most “yes” answers, the clearest documentation and the fewest excuses.
- Walk away when necessary. If a contractor becomes defensive, dismissive or refuses to provide proof, that is often the only clue you get before problems show up on your property.
Questions To Ask A San Diego Outdoor Living Contractor
If you do nothing else, ask these questions on your next contractor call or site visit. They’re pulled directly from the checklist and will quickly show you who is prepared – and who is cutting corners.
- “What is your CSLB license number and which classifications do you hold?”
- “Do you carry workers’ comp for everyone who will be on my property?”
- “Can you send me your current liability and workers’ comp certificates?”
- “Who will manage my job day-to-day and what quality checklist do they use?”
- “How will you document base prep, drainage and utilities before everything is covered?”
- “Will I receive a written schedule with start date, phases and a clear completion window?”
- “How are change orders handled and priced, and will I see them in writing before work proceeds?”
- “Do you carry professional errors & omissions insurance for design and planning mistakes?”
Core Due Diligence Items (Compare Line-By-Line)
Below is a sample of what you will see inside the full checklist. Use this table as a quick reference when you speak with contractors. The PDF version includes additional items and space for notes for each company you are considering.
| Due Diligence Item | Why It Matters | Questions To Ask | IID Standard |
|---|---|---|---|
| Active CSLB License & Correct Classifications | Confirms the contractor is legally allowed to perform landscape, hardscape and turf work and has passed state requirements. | “What is your CSLB license number and which classifications do you hold?” | Active California license with landscape (C-27) and related specialty classifications (such as D-06 concrete-related and D-12 synthetic products). |
| Workers’ Compensation Insurance | Protects you if anyone is injured on your property. Without it, you can be held financially responsible. | “Do you carry workers’ comp for all employees and can I see a current certificate?” | Full workers’ compensation coverage for employees; certificates available on request. |
| General Liability Insurance | Covers accidental damage to your home, structures or neighboring properties during the project. | “What is the limit on your liability policy and who is the carrier?” | Liability coverage in the seven-figure range with reputable carriers and certificates provided for each project. |
| Licensed & Insured Subcontractors | Trades like grading, electrical, plumbing and gas must be performed by licensed subs to meet code and protect your warranty. | “Are all of your subcontractors licensed and insured for the trades they perform? Can I see proof?” | Every subcontractor we use is licensed and carries their own liability and workers’ comp insurance; documentation available. |
| Dedicated Project Manager & QA Checklist | Without a PM, crews are often unsupervised and critical steps get skipped, especially on drainage and base prep. | “Who will manage my job day-to-day and what quality checklist do they use?” | Dedicated PM on every project with a structured multi-point QA checklist and documented approvals at each phase. |
| Documented Subsurface Installation Proof | The most important parts of your project are buried. Photos of base prep, compaction, drainage and utilities are your long-term proof. | “Do you provide photo documentation of base, drainage and utilities before everything is covered?” | We photograph every critical subsurface phase and store it in your digital project record so there is no question how it was built. |
| Written Schedule & Milestones | A real schedule prevents endless delays, idle days and “we’ll be back next week” surprises. | “Will I receive a written schedule showing start, phases and expected completion date?” | Every project has a written schedule, milestone dates and a defined completion window backed by our On-Time Completion Guarantee. |
| Financial Stability | Contractors under financial stress are more likely to juggle deposits, cut corners on materials or abandon jobs mid-project. | “How do you fund materials and payroll? Are you relying on customer deposits to finish other jobs?” | We operate from a position of financial strength – materials are purchased upfront or in real time and crews are paid weekly, not with deposits from other jobs. |
| Clear Change Order Policy | Vague verbal changes are a common source of surprise charges and disputes once construction is underway. | “How are changes handled and priced? Will I receive written confirmation before extra work is done?” | All changes are documented in writing with pricing approved before work proceeds so there are no mid-project surprises. |
| Daily Documentation & Live Project Tracking | Daily photos and notes keep you informed and create a permanent record if questions ever arise in the future. | “How will I see progress and communicate during the job? Do you use a project portal or tracking system?” | We provide daily documentation that feeds into a live project tracking portal so you always know what was done, what’s next and who is on site. |
| Professional Errors & Omissions Insurance | Protects you if there is a mistake in design, planning or administration that leads to financial loss. | “Do you carry E&O insurance for design and planning, and what does it cover?” | We carry professional E&O coverage to back our design-driven projects and protect clients from planning errors. |
| On-Time Completion Guarantee | Most delays are shouldered by the homeowner. A written schedule guarantee flips that accountability back onto the contractor. | “Do you guarantee your completion date in writing and compensate me if you miss it?” | We offer a written On-Time Completion Guarantee and put real dollars behind it if we’re late (with clearly defined exclusions). |
| Dedicated Multi-Layer Support Team | Having only one contact who “might pick up” leads to stalled projects and poor communication. | “If I need help during the project, who can I reach and how quickly do they respond?” | Your Senior Designer, Project Manager, Operations Manager and General Manager all know your project and can step in if someone is unavailable. |
| Employee Background Checks | You are inviting crews into your home and yard. Rigorous screening protects your family and property. | “Do you run background checks on employees who will be on my property?” | We require federal and state background checks for employees so only vetted, trusted team members work at your home. |
The full PDF includes additional items around years in business, crew experience, certifications, reviews and warranty support so you can compare contractors with complete clarity.
Big Red Flags – When You Should Walk Away
As you work through the checklist, some answers matter more than others. If you see several of the red flags below, it is usually safer to keep looking, even if the price looks attractive.
- No workers’ comp or proof of insurance. If someone is hurt on your property, you may be the one paying the bills.
- Vague scopes, allowances or “we’ll figure it out later.” These often turn into costly change orders once the job is underway.
- No documented subsurface work. If they cannot show you how they build the base, drainage and utilities, they probably are not doing it consistently.
- No dedicated project manager or written schedule. “We’ll be here when we can” almost always leads to stop-and-start work and extended timelines.
- Unlicensed or uninsured subcontractors. This puts your permits, inspections and personal liability at risk.
- Unrealistic, marketing-style warranties. Extremely long installation warranties with lots of fine print are often less protective than a realistic, enforceable one.
- Reluctance to answer questions or provide documentation. A good contractor is proud of their processes and happy to show how they protect you.
If you’d like a second set of eyes, we can review your bids with you on a quick call. We’ll walk through your checklist line-by-line, flag missing drainage or subsurface details, and point out any red flags we see. No pressure and no obligation to hire us.
Most reviews take 5–10 minutes and often save homeowners from five-figure mistakes.
Real-World Example – When Shortcuts Show Up Later
Here is a typical scenario we see in San Diego:
A homeowner hires a low-bid contractor to install new pavers and turf. The price looks great and the surface looks fine on day one. There is no written drainage plan, no photos of the subsurface work and no project documentation.
During the first heavy rain, water collects against the house and backs up through the new turf. The paver field begins to settle because the base was thin, poorly compacted and lacked proper underdrains. Repairs require demolition, new base, new drainage and new turf.
By the time everything is corrected, the total cost to “fix the savings” is well into five figures – several times the difference between a low bid and a properly engineered install.
This is exactly the type of situation the checklist is designed to prevent. When you ask the right questions up front and require proof, shortcuts are much easier to spot before they are buried under concrete, pavers or soil.
FAQs – Using This Checklist in San Diego
Do I need to use this checklist even if I already know which contractor I like?
Yes. Even when you have a favorite, verifying licensing, insurance, drainage practices and financial stability protects you from surprises later. It only takes a few minutes to confirm you are making a safe decision.
What insurance should a San Diego outdoor living contractor carry?
At a minimum, look for active workers’ compensation coverage for employees and general liability insurance with meaningful limits. For design-heavy projects, professional errors and omissions coverage adds another layer of protection.
How many bids should I compare with this checklist?
Most homeowners compare two or three contractors. The goal is not to collect as many numbers as possible, but to see who can clearly demonstrate compliant installs, strong documentation and predictable scheduling.
What is the biggest red flag you see on San Diego bids?
The most common problem is vague or missing drainage and subsurface details. If a proposal does not explain how water will be managed and how the base will be built, it is difficult to know whether the project will last.
Can INSTALL-IT-DIRECT help me review other bids?
Yes. We are happy to provide a quick, no-pressure bid sanity check. We can walk you through the key items on your checklist and point out risks or omissions we see so you can move forward with confidence.
Always verify parcel-specific overlays, easements and permit requirements with the City or County before construction begins. This article is for educational purposes and is not a substitute for project-specific engineering or legal advice.