The STR Loophole

About · Keith Haughton, Founder

I built the roadmap I couldn't find.

ViaSTR makes short-term rental investing more accessible, efficient, and empowering — for busy professionals who want real numbers and a clear sequence, not scattered advice from people selling property.

Keith Haughton Written by Keith Haughton · Founder, ViaSTR

Why this exists

Hi, I'm Keith. My route into short-term rentals started with a simple question: how do I grow wealth, protect my time, and stop depending on a single paycheck?

Along the way I learned about strategies that let short-term rental investors unlock real financial benefits — provided they run the properties the right way, and document it.

With a growing family, sustainable income and long-term security stopped being abstract goals. I wanted a roadmap that combined real-world experience with clear, actionable steps. What I found instead was scattered advice, contradictory threads, and a steep learning curve with no obvious first rung.

That gap became ViaSTR.

Background

From tech to STR strategy

I've spent over 15 years building and delivering complex solutions in technology services — across product development, customer success, sales engineering, and strategic planning for enterprise clients.

Even with that foundation, getting started in short-term rentals wasn't simple. The information was scattered and the learning curve was steep. If it was that hard with a background in breaking down complicated systems, it was going to be harder for everyone else.

So I started writing it all down. That's what you'll find across this site.

Pragmatic Marketing Certified Strategy & Innovation — MIT Sloan Automation Data analysis Process optimization

What ViaSTR is

A content hub, a community, and a referral network.

Built for busy professionals stepping into STR ownership — whether you want to run your first property hands-on or assemble a team of experts to do it with you.

Teach

The mechanics, end to end

How STR investing and day-to-day operations actually work — acquisition, qualification, running the property, and what the return looks like at the end of it.

Connect

Tools and experts

The software, services, and specialists worth your time, with an honest note on where each one fits and where it doesn't.

Share

Real examples

Case studies, checklists, and field notes from properties that are actually operating — including the parts that went sideways.

Introduce

Vetted providers

A growing network of service providers we've checked out, so you're not picking a CPA or a cleaner from a search result.

My promise

Understand what's working now. Then use it.

We're starting with a blog and a resource library. Membership is free, and it stays free — no course, no upsell ladder.

Create a free account
01Our most useful tools, as they're built
02Educational content on qualifying, operating, and staying compliant
03Partner deals and vetted referrals
Keith Haughton, founder of ViaSTR

Come say hello

If you're weighing your first property, stuck on whether you qualify, or already operating and unsure what to document — that's exactly what this site is for. Send me a note, or find us in the places below.

— Keith Haughton, Founder, ViaSTR

ViaSTR is educational. Nothing here is tax, legal, or investment advice, and no article or tool creates a client relationship. Tax treatment of short-term rentals depends on your own facts — how the property is used, how you participate, and what you can document. Talk to a qualified CPA or tax advisor before you act on anything you read here.