WELCOME TO empowered INVESTING.

Helping everyday investors make smart, informed decisions—with clear, unbiased guidance.

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Money blinds. Charisma sells. And the truth fades behind a quick deal.

The numbers are sugarcoated. Red flags are downplayed.
The pitch sounds good — until reality hits:

You’ve drained your savings to make someone else rich.

Here at HeadSight we are your second set of eyes.
When you're about to invest in a property, we step in as your trusted third-party advisor — helping you understand the deal before you sign anything.

We’re not brokers. We’re not trying to sell you anything. We’re here to protect you — by reviewing your deals, running the numbers, and helping you ask the questions no one else will.

חכם עיניו בראשו

Invest with insight, not impulse

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"Risk comes from not knowing what you're doing." - Warren Buffett

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Wise investors learn before they leap

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"An investment in knowledge pays the best interest." - Benjamin Franklin

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"Risk comes from not knowing what you're doing." - Warren Buffett 〰️ Wise investors learn before they leap 〰️ "An investment in knowledge pays the best interest." - Benjamin Franklin 〰️

HeadSight Real Estate Guidance was born from a simple — but painful — truth: too many people in our community lost their life’s savings chasing a promise — not a plan.

We saw it happen over and over again. Hardworking people with savings set aside, looking to invest in property to build equity and a better future… only to find themselves in a money pit.

They trusted a friend. A broker. Someone who “knew a guy.” But the broker made his commission and walked away. And these families were left stuck — bleeding cash every month on a deal that didn’t make financial sense from the start.

Over time, many of them came to us — sometimes in frustration, sometimes in tears — asking what went wrong. The answer was always the same: no one had their back at the beginning.

That’s why we started HeadSight.

We built this service to serve our community, plain and simple. Because we’ve seen too many people go in clueless— and we believe real estate should be a smart investment, not a trap.

If we can help even one person avoid a bad deal, we’ve done our job. If we can help many build solid, profitable portfolios — that’s our greatest success.

My name is Chaim Schechter. I’m a person who believes in helping others, in honesty, and in doing good. I’m not here to sell you anything. I’m here to give you clarity, so you can move forward — or walk away — with confidence.

Built on Experience. Driven by Integrity.

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“Knowledge isn’t just power; It’s peace of mind, smart choices, and BE”H a secure future.”

– Chaim Schechter, HeadSight RE Founder & Advisor

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what we do:

Financial Deal Breakdown

We go through the financials— income, expenses, cash flow, and returns — so you understand what the deal is really worth.

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Full Due Diligence Review

We take a hard look at the details: lease terms, financing, inspections, and red flags others might miss.

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Neighbor-hood & Market Analysis

We research the area, comps, trends, and tenant demand to see if the location makes sense long-term.

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honest advice with no agenda

We offer strategic guidance on deal viability, risk factors, and investment alignment — tailored to your financial goals.

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how it works

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send us the deal

Just upload or email us the listing or deal info you’re considering.

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we analyze & advise

We run the numbers, review the comps, and flag any concerns or hidden issues.

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you decide with ease

No pressure, no commission. Just clarity.

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ready to review a deal?

Let’s protect your investment — before you make it.

 FAQs

  • No — and that’s intentional. We don’t make a dime if you buy or walk away. We exist to give you an honest, outside perspective.

  • Anyone with some savings, a job, and no time to become a full-time investor — but who wants to make a smart move in real estate.

  • Typical turnaround is 2–3 business days. Faster reviews available upon request.

  • Yes. We offer bundle pricing for active investors.

  • Yes. We advise on both residential and commercial real estate deals — from single-family homes to multi-family units, small mixed-use properties, and commercial investments. Whether you're purchasing your first rental or considering a more complex opportunity, we provide the insight and due diligence you need.