Multi family or short term rental?

[Cam Crafty]

Looking to buy my first investment property and I'm torn between buying a somewhat expensive short term rental in a coastal area or a multi family in a mid size city. I know a multi family is easier to pay down and will probably give me some cash flow in the first year, but I love the idea of owning property someplace I want to vacation or retire. Long term goal is to have 4-8 properties generating cash flow with at least 2 paid off before I retire (in 10-15 years)

What are the pros and cons of each? What's the smartest choice?

[Mohammed Rahman]

We all want the “nice to haves,” but there’s a big difference between what feels exciting and what actually works as an investment. The whole point of an investment property is to make money and give you stability, not just check lifestyle boxes.

You can definitely find something that gives you a mix of both, but I wouldn’t lead with the emotional side. For a first deal, it’s usually smarter to focus on what meets your financial goals, brings in steady income, and keeps things predictable. Your first property is where you learn how everything works, so you don’t want extra complications on top of that.

A multifamily in a mid‑size city tends to be more predictable, easier to finance, and a cleaner path to building a portfolio. A short‑term rental in a vacation market can work too, but it comes with more moving parts like seasonality, regulations, and more hands‑on management than people expect.

At the end of the day, you’re trying to build toward a handful of properties and long‑term cash flow. The best first step is usually the one that keeps things simple, reduces surprises, and helps you stay in the game long enough to grow.