First Step When Buying an STR

[Ryan Moyer]

This has been on the top of my mind a lot lately, with a lot of the clients I've interacted with. I always ask them about their goals first, and it always shocks me how often people don't have an answer to it.

One of the top mistakes people make when both buying and operating STRs is not properly defining their goals, and adjusting their expectations to match.

Are you buying purely for ROI/returns? For long term appreciation/wealth building? For tax advantages? For personal use and just some rents to supplement that on the side?

Not only are these completely different buy boxes in your search, but also completely different operating approaches.

Currently I buy for returns. So I optimize for returns, even if that means I am going to slash prices last minute, or fill 1 night gaps, or just generally run at a higher occupancy with more wear and tear. Yes it's cool to own a 3/4 size x-wing, but that's not why we built it.

But then I meet buyers who want to run their place like it's 2005. Week long bookings. High prices or sit empty. Zero risk. You can still do that, but you have to adjust your mindset. Guests own the experience on Airbnb right now and if you aren't willing to play ball you will underperform. The comps you used when underwriting aren't comps if they operate in riskier ways that you're not willing to. That's just reality.

I get this all the time when people see our numbers in Kissimmee (most saturated market in the country). $130 - $170k annual gross on $550k -$750k purchases. They ask why they are so far behind. And while part of it is the 4 pillars of optimization I've built up (amenities, rev management, listing optimization, direct marketing with nurture), a big part of it is just that they're not willing to optimize for revenue in the way that is demanded in 2026. If they used me as a comp when underwriting but want to operate like it's 2005, I was a poor comp, because we have different approaches for different goals. Many new buyers to the STR market want to have their cake and eat it too. That's just not the reality any more. You have to pick your priority, and note that it's probably going to negatively impact those lessor goals.

[John Underwood]

I like the 4 Pillars!