The Short Term Rental Loophole is a tax strategy that may allow depreciation losses from a short term rental to offset your W-2 income directly, rather than just passive income like traditional rentals. To potentially qualify, your property must average 7 days or fewer per stay and you must meet IRS material participation tests. A cost segregation study can then accelerate depreciation so you may be able to claim a larger portion of deductions in year one. When structured correctly with a qualified tax professional, this strategy has helped some investors create significant paper losses and tax savings. Tax outcomes vary based on individual circumstances and are not guaranteed. Always consult with a qualified CPA or tax attorney before making investment decisions.

Tax savings depend on your income level, tax bracket, property purchase price, how you structure material participation, and other individual factors. Some clients in the Accelerator have reported reducing their taxable income by $100,000 to $250,000 in a single year, though results vary significantly based on individual circumstances. During your free strategy call, we'll discuss your goals and how the program works. For specific tax projections, you can work directly with our vetted tax professionals who can analyze your unique situation.

No prior experience is required. The Accelerator is designed for high-income professionals, retirees, and investors who are new to short term rentals. Jane guides you through every step of the STR acquisition and launch process, from market selection and property acquisition to remote setup and automation. You'll also have access to the step-by-step digital course plus a vetted professional network, including tax professionals, so you're working with experts who understand this strategy.

During the 6-month program, you'll attend weekly group coaching sessions and may have occasional 1:1 calls as needed. Once your STR is operational, the automation systems reduce ongoing management to about 1 hour per day. If you prefer to be completely hands-off, Jane's co-hosting team can manage day-to-day operations for you.

No. The entire acquisition, setup, and launch process can be completed remotely. You can do video walkthroughs with your agent, work with vetted designers who have local installation teams, and coordinate professional photography without flying out. Many clients never visit their property and still achieve excellent results with their STR operations.

That's exactly what the 1:1 STR Market Selection Strategy Session is for. Jane will help you define your purchasing power, then use her AI-assisted research framework to evaluate markets across long-term viability, regulation risk, and property types that perform well. You'll leave with a clear recommendation on 1-2 target markets and the exact property profile to pursue.

After you enroll, you'll receive immediate access to the program materials, digital course, and community. You'll then schedule your 1:1 Market Selection Strategy Session with Jane to begin identifying your target markets. From there, you'll join weekly group coaching calls and have on-demand access to Jane whenever you need guidance on STR decisions, obstacles, or next steps. You'll also be connected with tax professionals in our network to discuss the tax strategy component.

With Jane's vetted professional network and acquisition support, many clients get under contract within 60 days of starting the program. The entire process from enrollment to first booking can happen within 4-6 months, depending on your market and how quickly you move through the acquisition process.

If you already own rental properties, you may be able to convert an existing property or acquire a new one specifically structured for the STR strategy. Jane can help you understand the STR criteria and connect you with professionals who can evaluate your current portfolio and goals. Your tax professional will ultimately determine whether your current properties could qualify or if acquiring a new property makes more sense for your situation.

When structured correctly with qualified tax professionals, the Short Term Rental Loophole is a legitimate tax strategy that has been used by many investors. The risk comes from not meeting material participation requirements or improperly documenting activities. The Accelerator provides documentation templates and activity tracking systems to help you stay organized for your tax professional. Your CPA or tax attorney will confirm your qualification and handle any IRS-related matters.

If you prefer not to manage the STR yourself, Jane's co-hosting team can handle all day-to-day operations for you. You'll simply monitor performance and enjoy the cash flow while the team handles guest communications, turnovers, and maintenance coordination. This option is perfect for busy professionals who want the investment returns without the operational involvement.

Most CPAs and financial advisors are not trained in short term rental acquisition and may not know what property criteria to look for. The Accelerator provides education on how the STR Loophole works, plus the complete execution system for acquiring and launching your property: market selection, property acquisition support, vetted professional network, remote setup, and automation. You'll then work with qualified tax professionals in our network who handle the actual tax strategy and compliance. You're getting both education and implementation support, not just advice.

You'll have multiple layers of support throughout the program. Weekly group coaching sessions address common questions and challenges related to STR acquisition and operations. On-demand 1:1 calls with Jane are available whenever you hit a key decision point or roadblock. The private community allows you to post questions and get feedback from Jane and other members at any time. For tax-specific questions, you'll work directly with the tax professionals in our vetted network.

And if you prefer to learn independently (or want a place to revisit something later), you’ll also get access to the full digital course that covers everything step-by-step. That way you can move at your own pace, rewind and rewatch the exact lesson you need, and refresh your knowledge anytime.

After the program, you should have a fully operational, semi-automated short term rental generating cash flow. You'll retain lifetime access to the frameworks, templates, and community. Many clients choose to continue in the program based on their needs, acquiring additional properties over time and working with their tax professionals to keep leveraging this strategy as part of their overall financial plan.

The Short Term Rental Loophole is often most impactful for high-income W-2 earners because it may allow depreciation losses to offset active income directly. However, retirees with investment income and real estate investors looking for cash-flowing properties can also benefit from the STR acquisition and automation training. During your strategy call, we'll discuss your goals and how the program works.

You're a good fit if you're a high-income professional interested in acquiring a short term rental, a retiree with funds looking for new ways to invest, or a real estate investor seeking cash-flowing properties. You should have the capital for a down payment and be willing to commit to the 6-month program. If you're ready to take action and want expert guidance on the STR acquisition process, this program is designed for you.

We discuss program investment details during the free strategy call after we've determined that this is a good fit for your situation and goals. The call allows us to understand your specific circumstances and explain how the program works before discussing next steps.

Scroll up and click the button to book your free strategy call. On the call, we'll discuss your goals, explain how the STR Loophole works, and answer any questions you have about the program or timeline. By the end, you'll know exactly how the program works and whether it's a fit for your situation.