What Your Insurance Agent Isn’t Telling You

Everyone says they hate insurance.

I used to say so, too. 

Then I started wondering if “hate” was really just a cover story for “don’t understand.” The people I’ve seen get burned by insurance usually didn’t read the fine print, didn’t have their policies clearly explained, or didn’t know what questions to ask in the first place. Then, when it came time to file a claim, what they didn’t know hurt them.

I recently sat down with Zach Vaswani, an insurance agency owner based in Norwood with a decade of experience helping people protect their assets and save money. We had the conversation most house hackers skip. This is what came out of it.

I’ve known Zach since elementary school.

Thirty years of friendship and a “couple” of beers later, it’s safe to say I trust him. But my confidence in Zach goes beyond knowing him forever.

Before opening his own brokerage, he spent years selling to and working directly with insurance companies. He saw the industry from the outside first, noticing which agencies were sharp, which ones were sloppy, and what separated good advisors from people just trying to write another policy.

Now he sees the other side as a brokerage owner. He trains his team, stays plugged in with other professionals, and keeps sharpening how his agency advises clients. He’s a lifelong learner in an industry where most of us are just trying to understand what the hell we’re even paying for.

That’s why I call him whenever I have insurance questions.

He’s never pressured me to use him. He’s always led with the relationship, not the sale. And selfishly, I’m glad I do use him because he’s saved me a bunch of money over the years!

More importantly, I’ve learned a lot from him. 

Insurance has always felt like smoke and mirrors to me. Zach cuts through the crap and explains what matters, what doesn’t, where people overpay, and where they accidentally leave themselves exposed.

According to Zach, the two main drivers of price: dwelling coverage and your deductible.

Dwelling coverage is what it would cost to rebuild your home from scratch (not your purchase price). Insurance agents use a replacement cost estimator that accounts for square footage, heating system, siding, roof material, and finish quality.

The goal is to get it right. Zach said you can do this “by being super detailed and explicit about everything in your house. That way, when an insurance agent writes it up, he or she has as much information as possible to get you the exact coverage you need.” Too little and you're underinsured when it matters most. Too much and you're overpaying for a ceiling the insurer won't pay out anyway. 

Your deductible is what you pay out of pocket before insurance kicks in. Higher deductible, lower premium. Lower deductible, more protection upfront. Zach's take: “match your deductible to your cash position. Strong reserves? Go higher and pocket the difference. Running lean? A lower deductible gives you a softer landing when something goes wrong.”

Turns out, I’ve been asking the wrong question. 

The real question is whether the person you're working with understands your situation and can customize a policy based on your specific needs. You want someone who's going to pick up the phone when something changes, ask the right questions before you sign anything, and stick around long enough to see how your needs evolve.

Real estate is a long game. Your insurance relationship should be, too.

The value of a good agent isn't finding you the lowest premium. It's having someone in your corner who knows your property, knows your goals, and can tell you when your coverage needs to change before a claim makes that decision for you.

That kind of relationship doesn't come from a comparison website or a call center. “It comes from a referral — someone in your network who owns investment property and found a person they actually trust. Ask around before you default to whoever pops up first in a Google search,” he noted.

When you do find that person, tell them everything. Not just the basics. Tell them how you're using the property now, how you plan to use it in the future, and what you're not sure about yet. A good agent will use that information to advocate for you. A bad one won't ask.

Before you fall in love with a deal, know what can create insurance problems down the road. This matters more than most buyers realize because your mortgage lender requires the property to be insurable before they'll fund the loan. No insurance, no closing. 

These are the two issues Zach said carriers flag most often:

1. Roof age and condition: This is the big one. Carriers may require a full replacement, or at least treatment for moss and lichen, before they’ll write a policy. An old or damaged roof signals risk, and insurers price accordingly. If the inspection flags the roof, don’t brush it off…it could affect your ability to get coverage at all.

2. Knob-and-tube wiring: If you’re buying in a market that has older housing inventory like most of New England, pay attention to this. Knob-and-tube is considered a fire risk, and many carriers simply won’t cover properties that have it.

Some carriers will, but your options get narrow fast and your premium will reflect it. If you’re buying an older property, get clarity on the electrical system before you’re under contract, not after.

Neither issue is automatically a deal-killer. But both are things you want to know before closing.

Sometimes a property with an old roof or knob-and-tube wiring is actually worth buying (if the numbers make sense). These issues spook a lot of buyers, which means less competition and a bigger discount at the negotiating table. If you know who to call, understand what it'll cost to fix, and are willing to take it on, that problem property might be exactly the kind of deal that works in your favor. Just go in with your eyes open, a real estimate in hand, and a contractor you trust lined up before you close.

The time to find out isn’t when you’re trying to bind coverage two days before closing.

This is where house hackers run into the most expensive misunderstanding.

You buy a property, live in it, rent out a unit or some rooms, and eventually move out. At some point, the property becomes a full rental. When that happens, your standard homeowners policy doesn't cover you anymore.

A homeowners policy is written for an owner-occupant. Once the property becomes a rental, you need a landlord policy built for the actual risk profile of a rental. Here’s what that means in practice:

The policy you need when you move in is not always the policy you need when you start renting units. Treat each transition like a coverage event, call your agent before the change happens, and plan accordingly.

Zach prides himself on being able to save customers money on insurance. Here are some suggestions that can save help you keep more in your pocket:

There’s a big difference between grabbing the cheapest quote just to close, getting screwed over later, and actually understanding what you’re buying.

Your property use can change fast. You might move in, rent out a unit, rent by the room, renovate, move out, or turn the place into a full rental. Your coverage needs to keep up.

One question worth asking yourself before your next closing: do I actually know what this policy covers, or am I just hoping nothing goes wrong?

If the answer is the second one, that’s where to start. Review your policy with an insurance provider you trust. Don’t have one? Reply “contact Zach” and I’ll connect you. Share it with someone who needs to hear this.