For High-Income Investors
High Income, Big Tax Bill, Few Deductions Left?
If you've maxed out your retirement accounts and you're still writing large checks to the IRS, a professionally managed short-term rental may help offset your income through depreciation, while building long-term wealth. We guide you through acquiring and setting it up, then manage it for the long term. You own the asset.
Informational only: not tax, legal, or accounting advice. Consult your own tax advisor before investing.
The Problem
You've Done the Smart Things — and Still Owe a Fortune
A properly structured short-term rental may create meaningful depreciation opportunities while building long-term wealth. Whether it fits your situation is a conversation for you and your tax advisor. We make the real estate side work.
The Opportunity
How a Short-Term Rental Can Work in Your Favor
Own a Real Asset
Not a fund or a paper position — an actual property in a proven market, held in your name or your entity, that can appreciate over time.
Build Rental Income
A well-placed, professionally managed rental earns from bookings year-round. Like any new listing, it ramps as it gains reviews and ranking. Getting there quickly and keeping occupancy high is the management team's job.
Enjoy It Yourself
It's still your property. Block off the dates you want and use it as your own Mt. Hood or Portland getaway, then let it earn the rest of the year — your CPA will weigh in on how personal-use days affect the tax picture.
Depreciation May Offset Income
Short-term rentals are often discussed alongside cost segregation and bonus depreciation. Whether any of it applies to you is your CPA's call. We make the underlying real estate work.
Depreciation and tax treatment depend entirely on your individual circumstances and applicable law. This is not tax advice; consult your own CPA or tax advisor.
Hands-Off, Long-Term
You Invest. You Don't Become a Landlord.
We Find the Property
We identify properties suited to short-term rental performance in Portland and Mt. Hood submarkets that actually perform, and steer you away from the ones that don't.
We Set It Up With You
Our furniture and home-staging companies do the heavy lifting. In year one you make the calls (which is what earns the tax benefit) and we handle the legwork.
We Manage It
Your property joins a management operation running 300+ short-term rental doors. Bookings, guests, cleaning, and upkeep are all handled.
You Own It
Title is in your name or your LLC. The asset is yours, the income is yours, and you build equity as the loan pays down.
We Report
You receive clean operating and income reporting: everything you and your tax advisor need at tax time.
No 2 A.M. Calls
No guest messages, no cleaning crews to chase, no maintenance emergencies landing on you. That's the whole point.
One honest exception — year one. The first-year tax benefit is earned by taking an active, documented role in the setup and first season: choosing finishes, launching the listing, handling the first bookings. We hand you a simple playbook and time log to make it straightforward, then we take over and it's hands-off for good. Your CPA confirms what's needed for your situation.
Don't Take Our Word For It
An Operating Network, Not a Sales Pitch
Every part of this is a real, reviewable business you can stand on — management, booking, design, and furnishings. Click through and see for yourself.
Management
Simply VRM
Full-service short-term rental management.
300+ doors managed · since 2014 · 60,000+ guest reviews
Direct Booking
Stay Portland
Our direct-booking brand for Portland homes.
80,000+ guests · 4.8★ (12,400+ reviews) · City-permitted
Cabins & Mountain Homes
Mt. Hood Basecamp
Cabins & mountain homes across the Mt. Hood corridor.
Government Camp · Welches · Rhododendron · Sandy
Staging & Design
Greylyn Wayne
Home staging & interior design.
2,500+ homes staged · 4× Street of Dreams · 4.9★
Furnishings
What's New Furniture
Furniture & furnishings showroom.
25,000 sq ft showroom · 4.8★ (400+ reviews)
Real Numbers, Live Pipeline
See What We're Underwriting Right Now
We're constantly underwriting Mt. Hood-corridor short-term rentals against the real trailing-12-month performance of homes we already manage. Here's a representative example of the kind of deal we bring investors, and the live pipeline changes every week.
Representative Deal
Mt. Hood corridor · 5 bd / 4 ba
~$1.05M
Projected cash flow
+$1,550/mo
expected case
Est. year-1 tax savings
~$95K–$107K
land-excluded, @ 37%
All-in to start
~$473K
35% down + setup
Representative and illustrative: not a specific offer or a guarantee. Expected case after management, operating costs, and financing at 35% down / 6.75%; the conservative case runs near break-even. Tax figures are land-excluded at the 37% top federal rate and depend on your income, material participation, and a qualified cost-segregation study. Consult your own CPA.
The Live Pipeline
Want to See What We're Underwriting Today?
The pipeline moves fast, and every investor's fit is different. Tell us what you're looking for and we'll send the specific homes we're underwriting right now, with the full conservative-to-upside proforma for each.
See This Week's DealsHow It Works
From First Call to Managed Investment
One conversation gets it started. We handle the rest and keep you informed.
Strategy Call
We learn your goals, timeline, and budget, and if you have a CPA, we coordinate with them from the start.
Property Acquisition
We identify and help you acquire a property suited to short-term rental performance in a proven Portland or Mt. Hood submarket.
Setup & Furnishing
You lead the first-year setup with our support: our furniture and staging companies do the heavy lifting to get it guest-ready.
Professional Management
The property joins a management operation running 300+ short-term rental doors across Portland and Mt. Hood.
Ongoing Reporting
You receive the operating and income information you and your CPA need to file at tax time.
I Use This Myself
“I don't just sell these — I own and run one myself. I brought in a cost-segregation firm, placed it in service, and accelerated tens of thousands of dollars of depreciation into year one. That's why I can guide the parts that decide whether this works for you: the right property, getting it in service in time, and running it well. Exactly how the deduction applies to your situation is a conversation for you and your CPA, and we work alongside them.”
Jacob Serrill
Broker · Kelly Right Real Estate
Reflects my own experience; not a prediction of any investor's tax result. Consult your own CPA.
Your Advisor Stays Central
We Work Alongside Your CPA
Already have a tax advisor? Perfect. We never give tax advice: we keep your CPA in the loop with clean reporting so they can do their job and keep you optimized. Don't have one yet? We can introduce you to advisors who understand this strategy well.
Are you a CPA yourself? See how we partner with advisorsCommon Questions
FAQ
Do I have to manage anything?+
Ongoing, no. That's the core of what we do. The property is run by a management operation handling 300+ short-term rental doors, so bookings, guest communication, cleaning, and maintenance are all covered. The one exception is the first year: an active, documented setup role is what establishes the tax position, and we give you a simple playbook for it. After that, you own the asset and we run it.
How involved do I have to be in the first year?+
More than the years that follow — by design. To support the first-year tax benefit, you (or your spouse) take a hands-on, documented role setting the property up and running the first season: selecting finishes, building the listing, handling the early bookings. We provide a step-by-step playbook and a time log to make it manageable, and your CPA confirms what your situation requires. From year two on, it's fully managed and hands-off.
How much do I need to invest?+
It depends on the property, the market, and your financing. There's no fixed minimum: on a quick call we'll talk through your situation, your goals, and what makes sense before you commit to anything.
Is the income passive?+
The day-to-day operation is fully managed, so your involvement is minimal. Whether the activity is treated as passive or non-passive for tax purposes depends on your specific facts and how you participate: that's a question for your CPA, not us.
Is this tax advice?+
No. Nothing on this page is tax, legal, or accounting advice, and we don't provide it. We're real estate and short-term-rental professionals. Any depreciation or tax treatment depends on your circumstances. Rely on your own CPA or tax advisor for that.
What are the risks?+
All real estate carries risk, including loss of principal. Rental income and occupancy vary and are never guaranteed. We focus on submarkets with a real operating track record, but no investment is a sure thing. We'll be candid with you about the trade-offs.
Where are the properties?+
The Portland metro and the Mt. Hood corridor. That focus (and a management operation already running 300+ doors there) is part of why the properties perform.
Who You Work With
Your Point of Contact
Jacob Serrill
Broker · Kelly Right Real Estate
Jacob owns and operates short-term and long-term rentals of his own and works with a team that runs 300+ doors across Portland and Mt. Hood, plus contracting, furniture, and staging businesses that take a property from purchase to guest-ready.
Let's Talk
See If It's a Fit
Tell us a little about your situation and we'll set up a quick, no-pressure call to walk you through how it works and whether it makes sense for you. No obligation, no cost.
We typically reply within one business day. Your details stay private. No spam, ever.
This page is provided for general informational purposes only and is not tax, legal, accounting, or investment advice. Sell Portland Group and Kelly Right Real Estate do not provide tax advice. Any depreciation, deduction, or tax treatment depends on your individual circumstances and applicable law; consult your own CPA, tax advisor, or attorney before making any investment or tax decision.
No representation or guarantee is made regarding rental income, occupancy, returns, depreciation, or any tax outcome. All real estate investments carry risk, including loss of principal. Individual results vary.
Real estate brokerage services provided by Jacob Serrill, Broker · Kelly Right Real Estate · 1011 SE Oak St, Portland OR 97214 · (503) 780-7521. Short-term rental management is provided by an affiliated management group. Equal Housing Opportunity.