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May Homeowner Checklist: What You Should Be Doing Right Now

financial planning homeownership monthly maintainance May 15, 2026
expert mortgage explains what homeowners should do in May including insurance, escrow, taxes, and maintenance tips

If you own a home, May is one of those months where a few simple check-ins can save you a lot of money and stress later.

Most homeowners don’t think about this stuff until something goes wrong—and by then, it’s expensive.

If you’d rather watch or listen to the full breakdown, here’s the video:
https://www.youtube.com/watch?v=OX54lGnn2VI

Let me walk you through what you should actually be doing this month to stay ahead.


Make Sure You Actually Have Homeowners Insurance

I know that sounds obvious… but I’m not kidding.

I see this more than I should as a lender. We’ll be working on a refinance, ask for insurance, and the borrower says:

“Oh my god… it lapsed.”

That’s real.

And if something happens while you don’t have insurance, that’s not just stressful, that’s financially devastating.

So first things first:

  • Make sure your policy is active
  • Know when it renews
  • Don’t assume everything is fine

Track Your Renewal Date (And Start Early)

Once you confirm you have insurance, I want you to do one thing:

Add a reminder to your calendar 2 months before your renewal date.

I’ll give you a real example—this just happened to me.

I had the same insurance company for over a decade. Multiple policies. Paid on time every time. Did everything they asked to reduce risk.

They dropped me.

Just like that.

And now? The one quote I’ve gotten so far is three times what I was paying before—with less coverage.

That’s why I’m telling you not to wait.

If I had waited until the last minute, I wouldn’t have had time to shop, go through underwriting, or make any changes needed to even get insured.

And this isn’t just Florida or California; this is happening all over the country.

Start early. Always.


Compare Your Insurance to Your Escrow

If you have an escrow account (where your lender collects taxes and insurance monthly), I need you to check something.

Look at:

  • what your lender is collecting
  • what your actual insurance bill is

If those numbers don’t match, your payment will change.

Example:

  • Lender collects $1,200/year
  • Your actual policy is $1,600

That $400 difference?

You’re paying it. There’s no free ride.

So:

  • shop your insurance if needed
  • or start setting aside the difference now

And if you confirm the higher amount is correct, call your lender and have them update your escrow.


Check Your Property Taxes

Same idea here.

When your tax bill comes in:

  • open it
  • read it
  • compare it to what your lender is collecting

If taxes went up, your payment will go up.

If taxes went down, don’t assume your payment automatically adjusts.

And this part is really important:

Do not short-pay your mortgage.

Even if you think they’re collecting too much.

Keep paying the full amount until your lender recalculates it.

Because if you don’t, that payment can just sit there and not get applied correctly, and I’ve seen that spiral into major issues.

Just call them and say:
“Hey, I got my updated tax bill—can you re-run my escrow?”

Simple.


Don’t Wait for the News to Tell You to Refinance

If you’re waiting for headlines to say “rates are great,” you’re already late.

We’re in a market where rates move constantly.

Up, down, up, down—every week.

What we do for clients is simple:

  • we track where they are
  • we set a target rate
  • and when it hits, we call them

That’s how this should work.

It’s not your job to watch the market every day.


Stay Aware of Deed Theft (There Is Progress)

Quick update here—there is some good news.

Cities and states are starting to take deed theft seriously and put protections in place.

That’s a big deal.

But that doesn’t mean you ignore it; it just means things are moving in the right direction.


Handle Your AC Before Summer Hits

Please don’t wait until your AC breaks in July.

Because when it does:

  • everyone else’s is broken too
  • prices are higher
  • wait times are longer

May is the time to:

  • service it
  • change your filters
  • catch problems early

Even if you changed your filter recently, change it again.

It’s cheap. It matters.


Get Ahead on Seasonal Projects

Thinking about:

  • planting a garden
  • yard work
  • outdoor prep

Now is the time.

Same principle as everything else:
Earlier is easier and cheaper.


And One Last Thing…

If you have neighbors?

Maybe skip the wind chimes.

I’m just saying.


The Bottom Line

Owning a home isn’t just about making your mortgage payment.

It’s:

  • insurance
  • taxes
  • maintenance
  • planning ahead

None of this is complicated, but ignoring it gets expensive fast.

If you stay ahead of it, you avoid the kind of surprises that put people in bad financial situations.

And if you’re not sure how something affects your mortgage, your payment, or whether it makes sense to refinance, that’s exactly what we’re here for. We’ll walk through it with you, give you real answers, and help you make a decision that actually works for your situation.

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