And it's not choosing the wrong color
In fifteen years of painting homes across MetroWest Boston, I've seen a lot of mistakes. Homeowners who chose a color that looked great on a tiny chip but overwhelming on a whole wall. People who tried to paint over wallpaper instead of removing it. DIYers who got in over their heads.
But there's one mistake I see more than any other — one that costs homeowners thousands of dollars and months of frustration:
Choosing a painter based on price alone.
I get it. I really do. Painting isn't cheap, and when you get three quotes and one is 40% lower than the others, that's hard to ignore. You're looking at the same rooms, the same square footage. How different could the work really be?
The answer is: completely different. And I've spent years watching people learn this the hard way.
A Story From Last Spring
Last April, I got a call from a homeowner in Framingham. She was frustrated, almost in tears. Three years earlier, she'd had her exterior painted. She went with the low bid — a painter who came in significantly under everyone else.
The job looked good when it was done. For about two years.
Then the paint started peeling. Not just in one spot — in multiple places around the house. The south-facing side was the worst, but it was happening everywhere.
She called the original painter. No answer. Called again. No response. Looked up his business online — the website was gone.
So she called me.
I walked around her house and could see exactly what had happened. The prep work had been minimal. There were spots where old, failing paint had clearly just been painted over. The caulking around windows was cracking. In some areas, I could see they hadn't even cleaned the siding properly — the new paint had been applied right over dirt and grime.
This wasn't a paint failure. It was a preparation failure. The surface wasn't ready for paint, so the paint didn't stick.
My estimate to fix her house properly — including scraping all the failing paint, doing the prep work that should have been done the first time, and repainting — was actually more than her original quote. She was going to end up paying twice for what should have been done once.
I wish I could say this was unusual. It's not.
Why Low Bids Are Often Red Flags
Let me explain the math of painting, because it's important.
Paint costs what it costs. Labor costs what it costs. A professional painter needs to cover materials, pay their crew, maintain insurance, account for overhead, and still make a living. Those numbers are roughly similar for any legitimate painting business.
So when one quote comes in dramatically lower than others, something has to give. The paint isn't magically cheaper for that painter. Their workers don't work for free.
Usually, what's being cut is time — specifically, prep time.
Prep work is labor-intensive. It doesn't require expensive materials, but it requires hours. When a painter needs to lower their price significantly, skipping the sanding and priming steps is what usually leads to failure.
I've heard all the justifications:
- "The surface is already in good shape"
- "This paint is self-priming"
- "One coat will be plenty"
Sometimes these things are true. Often, they're shortcuts in disguise.
What "Cheap" Really Costs
Let's talk numbers, because this is where it gets real.
Say you're getting your exterior painted. You get three quotes:
- Painter A: $8,500
- Painter B: $9,200
- Painter C: $5,800
Painter C is tempting. That's $3,000+ in savings. But let's play out what often happens:
Year 1: Job looks great. You're happy you saved money.
Year 2: Some spots start fading. A little peeling on the sunny side.
Year 3: Peeling has spread. Neighbors are noticing. You know it needs to be redone.
Now you call Painter A or B (or someone like me). The quote to properly fix it — including all the prep work that should have been done originally — is $10,000+.
Your "cheap" $5,800 paint job just cost you $15,800 total. And you've spent three years living with a house that looked progressively worse.
Compare that to paying $8,500 or $9,200 upfront for work that lasts 7-10 years with proper preparation.
The cheap option wasn't cheap. It was the most expensive choice you could have made.
The Questions That Reveal Everything

When you're comparing quotes, the price isn't the only number that matters. Here's what I want you to ask every painter:
"Walk me through your prep process."
A good painter will get specific. They'll talk about washing, scraping, sanding, priming, caulking. They might even bore you with details about different surfaces requiring different approaches.
A corner-cutter will give vague answers. "We'll prep as needed." "We'll get it ready." These non-answers should worry you.
"How many coats are included?"
Two coats will outperform one coat in durability, protection, and color retention. Manufacturers like Sherwin-Williams specifically recommend two coats for their products to perform as designed. If a painter is quoting one coat to save money, that savings comes at a cost.
"What's your warranty?"
This tells you how confident the painter is in their own work. Anyone can say "we guarantee satisfaction." But will they put it in writing? Will they still be around in two years? Have they been in business long enough to honor a warranty?
At Paint Pro, we offer a two-year warranty on all painting work. We've been here fifteen years; we'll be here to honor it.
"Can I see examples of your work?"
Not photos from a website — actual homes you can drive by. Better yet, references you can call. A painter with a track record isn't afraid to share it.
Why I Don't Try to Be the Cheapest
I'll be honest with you: Paint Pro New England is rarely the lowest quote. Sometimes we're competitive. Sometimes we're in the middle. But we're not trying to undercut everyone else.
Because I know what it takes to do this work right. I know how many hours proper prep requires. I know what quality materials cost. And I know that if I cut those things to win jobs on price, I'd be setting homeowners up for exactly the kind of failure I've spent this whole article describing.
I'd rather lose a job to a lower bid than win it and do work I'm not proud of.
That might sound like a sales pitch, but it's genuinely how I feel. Fifteen years in, my reputation is the most valuable thing I have. Every house we paint is an advertisement — either for good work or bad work. I'm not willing to risk that reputation to be the cheapest option.
Making the Right Choice
If you're comparing painters right now, here's my honest advice:
Don't automatically go with the lowest bid. If one quote is significantly below the others, ask why. There might be a good reason — maybe it's a smaller crew with less overhead, or maybe they're just starting out and hungry for work. But there might also be a concerning reason.
Don't automatically go with the highest bid either. Price doesn't always equal quality. Some painters charge premium prices without delivering premium work.
Focus on process. Ask about prep. Ask about materials. Ask about experience. The painter who takes time to explain their approach and answer your questions thoroughly is usually the painter who takes time to do the job thoroughly.
Check references. Actually call past customers. Ask how long ago the work was done. Ask if they've had any issues. A paint job that looks good after three years is worth more than one that looks good after three days.
And if you'd like to get our perspective on your project, give us a call. I'll walk through exactly what your home needs, explain our process, and give you a quote that reflects honest work at fair prices.
Just don't choose based on price alone. It's the most expensive mistake I see homeowners make.
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David Griffiths