The one question that actually tells you whether an agent works with investors
After a round of coffee meetings, it's common to hear every agent describe themselves as investor-friendly before being asked, and just as common to then receive owner-occupant listings with a cap rate typed at the bottom, which doesn't actually demonstrate anything. The useful exercise is finding one short question that separates the ones who really do this work from the ones who just say it. Two schools of thought tend to disagree here. One says ask how many rental properties the agent owns personally, on the theory that someone who has never held a unit can't fully explain what a unit does. The other says ownership is beside the point and can even be a conflict, and what actually matters is whether the agent can underwrite fast and correctly on a property whose numbers are already known. There's also a references approach, asking for two investor clients who bought more than once, and a talk-me-out-of-it approach, where the real signal is whether the agent will ever tell a client a deal is bad. Of these, the underwriting test tends to be the most reliable in practice, since it's hard to fake in real time and doesn't depend on personal ownership history that may or may not translate to client-side skill.
Best single filter question for an investor-friendly agent?
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