8 Trick Questions to Ask “Investor-Friendly” Realtors

Every investor wants to find that “perfect” Realtor—the one who speaks fluent ROI, can spot a mispriced duplex before it disappears, and actually understands what a 1031 exchange entails. But as Greenville’s real estate market grows more complex, separating the truly investor-friendly from the simply investor-familiar has become a skill of its own.

In this episode of Selling Greenville, host Stan McCune shares eight revealing trick questions every investor should ask before hiring a Realtor. Each question tests not just knowledge but depth of experience—because in real estate, confidence without comprehension can be costly.

Trick Questions for Interviewing Investor-Friendly Realtors

The trick questions for interviewing investor-friendly Realtors aren’t meant to stump anyone; they’re designed to reveal how much a Realtor actually knows about the world investors live in—leases, cap rates, duplex shortages, and short-term rental regulations. As Stan explains, the goal isn’t to be tricky for the sake of it—it’s to gauge whether the person across the table can truly guide your investment strategy rather than guess through it.

1. “What CPA Would You Recommend for a 1031 Exchange?”

At first glance, it’s a straightforward question—but a seasoned Realtor won’t jump straight to offering names. They’ll pause and ask: Are you already under contract? What’s your timeline?

A 1031 exchange isn’t just about accountants; it requires a qualified intermediary and specific timing rules. A Realtor who grasps that complexity shows they’ve navigated real 1031 transactions before—and knows the pitfalls that can derail them.

2. “What Kind of Cap Rate Should I Expect?”

A cap rate is a handy metric in commercial real estate, but it doesn’t always fit small-scale residential investing. A knowledgeable Realtor should recognize that while cap rates can be calculated for duplexes or single-family rentals, they’re not the best comparison tool.

Stan reminds listeners that the 1% rule (monthly rent equaling 1% of purchase price) often provides a clearer picture for small portfolios. A Realtor stuck on cap rates might be using the wrong lens for the job.

3. “How Would You Help Me Find a Rental Before Buying?”

This one’s deceptively simple—and reveals how Realtors think. Many clients moving to Greenville need a short-term rental before purchasing. A strong agent will immediately ask about budget, location, furnishings, and pet policies.

The trap? Leaving those details out. Stan regularly sees agents posting vague requests like, “Looking for a rental—2,000 sq. ft., 4 bedrooms, small dog,” without mentioning price or area. Realtors used to the rental world know better; they think in monthly payments and specific parameters.

4. “What Are the Best Areas to Buy a Duplex In?”

Here’s where many Realtors bluff—and where experience shows. Duplexes, triplexes, and quads in Greenville County are rare. So when an agent confidently names a “hot area,” that’s a red flag. The truthful answer? There are a few on the market at any given time.

An informed Realtor will admit the scarcity and suggest alternative strategies, like broadening geographic criteria or setting alerts for new listings.

5. “If I Buy a Property with a Tenant Paying Below-Market Rent, How Do I Make Them Pay More?”

There’s only one correct first response: “What does the lease agreement say?”

That answer alone separates experienced investment agents from amateurs. Lease terms are binding, and understanding them is critical before making assumptions about raising rents. Realtors who skip that question likely lack hands-on experience managing tenant-in-place transactions.

6. “Where Can I Airbnb—and Where Can’t I?”

Short-term rentals are one of the most confusing topics in real estate. Even in Downtown Greenville, where restrictions are tight, Airbnb isn’t entirely banned—it’s just difficult.

An educated Realtor knows that rules vary by city limits and HOA covenants, and both tend to tighten over time. The right answer isn’t a yes or no—it’s a nuanced explanation rooted in local context and current regulations (because in Greenville real estate, “it depends” is practically a full sentence).

7. “How Much Does a Property Manager Cost?”

The rookie answer? “Ten percent of rent.”

The experienced one? “It depends—long-term or short-term rental?”

Stan notes that while 10% is a typical baseline, seasoned Realtors know that property management costs vary widely: 8% for long-term, flat-fee models, or much higher for Airbnb-style management. Realtors familiar with these distinctions are usually the ones who’ve actually worked alongside multiple managers and understand operational realities.

8. “Can I Get Traditional Financing on a Condo or Townhome for a Rental?”

This is the curveball question most Realtors fumble. In the Greenville MLS, condos and townhomes often appear side by side—but financing treats them as worlds apart.

Townhomes usually qualify for conventional or FHA loans with minimal issues. Condos, however, face a major hurdle: warrantability under Fannie Mae and Freddie Mac rules. If a condo’s HOA reserves or insurance don’t meet certain standards, traditional financing may not be an option.

Realtors who’ve closed condo deals before will know that the word “unwarrantable” can change everything—and that many buyers must pivot to specialized or portfolio loans instead.

Why These Questions Matter

Stan’s examples highlight a recurring truth: many Realtors call themselves investor-friendly without truly understanding investment mechanics. They may have sold a rental once or own a personal property, but that doesn’t equal mastery.

By asking the right trick questions, investors can quickly tell who’s fluent in the details that make or break deals—and who’s simply repeating buzzwords. More importantly, they can find partners who think ahead, understand risk, and navigate complex rules like 1031 exchanges, lease law, and financing nuances.

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Bottom Line

The trick questions for interviewing investor-friendly Realtors aren’t about testing trivia—they’re about revealing substance. Real estate investing isn’t just about listings and numbers; it’s about working with someone who knows how deals actually close, what red flags to avoid, and where the hidden opportunities lie (because no one wants a “fixer-upper” Realtor).

For investors looking to grow their portfolio in Greenville or beyond, the smartest move might start with a single question—the one that exposes who’s genuinely ready to guide them toward long-term success (and maybe save them from learning lessons the expensive way).

Ien Araneta

Journal & Podcast Editor | Selling Greenville