Every experienced investor remembers their first deal, and most will tell you the same thing: the questions you ask before you buy matter more than almost anything you do after closing. If you’re evaluating your first rental property, these five questions are a good starting filter.

First, what does the property actually cash flow, after realistic expenses — not just mortgage and taxes, but insurance, maintenance reserves, property management, and vacancy? Too many first-time investors underwrite optimistic scenarios and get surprised by real-world operating costs.

Second, who is the tenant profile in this location, and is that demand durable? A property near a single large employer carries different risk than one in a diversified job market.

Third, what is your realistic exit plan? Are you buying for long-term hold and cash flow, or are you underwriting a value-add play that depends on executing a renovation and re-lease strategy successfully?

Fourth, who is going to manage this property day-to-day, and have you honestly budgeted the time or cost that requires? Self-management sounds appealing until the first 2 a.m. maintenance call.

Fifth, and often overlooked: what happens if your assumptions are wrong? Stress-test the deal against a vacancy period, a major repair, or a slower rent-growth scenario than you’re hoping for. A good first deal isn’t the one with the highest projected return — it’s the one that still makes sense if reality falls short of the projection.