If I could go back, I’d have bought more investment properties before I upgraded my lifestyle.

I’ve funded hundreds of loans. I do this for a living. And I still made this mistake.

So when someone asks me whether they should buy a bigger home or an investment property first, I don’t answer like a loan officer. I answer like someone who’s living with the choice she made.

What I actually did

As my income grew, my life grew with it. A nicer home. A bigger renovation. The things that feel like a reward when you’ve worked hard for them.

None of that was wrong. But every one of those expenses comes out of my pocket today. If I’d bought investment properties first, some of those bills could be covered by something other than my paycheck.

Your home isn’t always the investment

Your home can grow in value. That’s real. But it doesn’t pay you every month. You pay it.

A rental is different. When it’s bought right, someone else helps pay it down, and it can put money back in your pocket. A bigger home makes life more comfortable now. A rental can make life more comfortable later.A bigger home is a reward. A rental is a plan.

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A Bigger home is a reward. a rental is plan.

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But not every rental is a good one

I’ll be honest: I own a rental that doesn’t cash-flow right now. Owning property doesn’t automatically make you wealthy. Buying the right property does.

I also came close to buying an investment property in Tennessee. On paper it looked great. When I ran the long-term numbers, it didn’t make sense, so I walked away. That was one of the better decisions I’ve made. Knowing when to say no is part of the strategy.

The questions I’d ask first

• Does it pay for itself? After the mortgage, taxes, insurance, repairs and empty months, is anything left?
• Can you carry it in a bad stretch? If it sits empty for a few months, does your life still work?
• Do you need the space now? A growing family or aging parents can make the bigger home the right call. Sometimes that home can include an ADU that does both.
• What do you want this to become? Think about what it means for your family in 20 years, not just this year.

If you already own

If you’ve owned for a few years, you may have more options than you think. Some people keep their current home as a rental and move up. Others use their equity to buy the investment first. The right answer depends on your numbers, and that’s worth looking at before you list.

So I’ll ask you what I wish someone had asked me: is your next move about how you want to live now, or what you want to build?