About Rent Bumper
The rental property landscape is messy. Short-term rental regulations change every few months. Tax rules seem to contradict IRS publications. Rent control keeps popping up like a disgraced zombie that may never die. Property management software promises to solve all your problems for $49/month (it won’t). And a lot of landlord blogs serve up recycled advice that doesn’t always account for the subtle nuances of this anything-but-passive type of investing.
I’m Devin, and I started Rent Bumper to cut through that noise.
Find me on LinkedIn or check out a couple of my properties: 🏝️ Wailea Oasis and 🪵 Boom Chalet.
This is a resource for DIY rental property owners who want straight answers about vacation rentals, mid-term leasing strategies, and traditional long-term rentals—written by someone who’s actually managed all three types and spent years professionally helping thousands of other landlords do the same.
Why This Site Exists
I started investing in real estate in 2006, back when you could list your vacation rental on VRBO for a flat $199/year and pay ZERO commissions! A lot has changed since then. Thanks Airbnb…
Fast forward to today: I own and self-manage five units across Hawaii and California—a mix of short-term vacation rentals, mid-term furnished stays, and traditional long-term leases. Before that, I spent years on the early team at Stessa (later acquired by Roofstock), where I ran Customer Experience and Content Marketing. In those roles, I talked to thousands of mom-and-pop landlords about their challenges as we built software tools to help them invest, own, and operate more efficiently.
Those conversations taught me something important: nearly everyone in this business has their own way of doing things. Two investors can look at the same underwriting and come away with completely different ideas about what to do next. One owner might be paying 2x what a similar investor down the street might pay for landlord insurance. Some landlords think DIY means replacing a water heater without hiring a plumber, while others won’t touch a light bulb.
Rent Bumper aims to close these knowledge and experience gaps, while acknowledging that every owner has unique goals and different risk tolerances. Even if you’re somewhat skeptical of the DIY approach to rental property investing, I suspect you’ll find more than a few ways Rent Bumper can help you. While we may sometimes compete with each other for the best acquisition opportunities, it’s also clear there’s a lot we can learn from each other.
What You’ll Find Here
Practical tips and best practices for all rental types – Whether you’re running short-term vacation rentals, mid-term corporate housing, or traditional residential leases, there’s something here for you.
Informational tax and accounting explanations – Rent Bumper covers depreciation, deductions, entity structures, and much more. It’s all written in English, not gibberish or high-finance dialect. None of our content is formal advice (get an actual CPA, attorney, or investment advisor for that), but everything we publish strives to be directionally useful based on real experiences.
Honest product reviews – Property management software, tenant screening services, and kitchen equipment are just the tip of the iceberg. I try to break down which services work best for which owners and which products you can skip altogether. I only recommend products and services that I genuinely believe will help rental property investors perform better.
Useful calculators and tools – Rent Bumper offers ROI models, depreciation worksheets, underwriting models, performance tracking templates, and other useful quantitative tools. This is the tricky spreadsheet stuff that is time consuming to build, but will ultimately help you understand what’s really happening under the surface.
What You Won’t Find Here
No fluff.
No expensive courses.
No hard sell on syndications.
No generic advice that treats all investors or properties the same.
How It Works
Everything here is free: the articles, the calculators, and The Bump, our occasional newsletter.
The site uses affiliate links, which means if you buy something recommended here, I may receive a small commission at no extra cost to you. The full disclosure can be found in the footer.
The Bump
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Get In Touch
Questions? Think something’s wrong in an article? Want to share your own landlord story? Want to partner up on some research, writing, or publishing?
Email: lordy(at)rentbumper(dot)com
Every message gets read, but individual responses aren’t always possible. Genuine questions and legitimate corrections will command my full attention. Mahalo!