When the numbers say one thing, but your instinct say another

[Jennifer Cornforth]

Hi guys, I have a quandary.

For my next real estate investment, I'd planned to purchase another condo in a complex with the husband and I already own. We have a short term rental there that is doing great, so we were going to double down. However, I've started to think about buying land further away instead, and then building several rentals on the land. (I live in Hawaii. And my island is extremely limited in what you can do for short term rentals. I'd be buying land elsewhere, where I could build and rent more freely.)

From a pure numbers perspective, buying 3 condos over the next few years makes more sense that buying 3 acres of cheap land and building 3 small rentals on the land. It's possible I'm overestimating building costs and underestimating what I could get for rent. But even so—I think condos are a better bet in the short-to-medium term. But.... I really like the idea of buying actual land.

We live on a half-acre, and we own a townhouse and condo we rent out. But maybe it's the Zombie-apocalypse prepper in me, but I like the idea of having something in our portfolio that's actual property, rather than just structures that will disintegrate over time.

Am I crazy for wanting to make the less lucrative investment? Or is the purchase of well-located land a good longer-term investment (like 20 years) and I'll be glad I have it in our portfolio?

Look forward to reading your responses.