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Posted Wednesday, December 10, 2025
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WCG’s Partnership With Evolve
Key Takeaways
- Material participation is absolutely possible with Evolve. Owners can stay in the driver’s seat even with a property manager, and when done correctly, STR rules can create real-time losses that offset W-2 and 1099 income.
- A free 40-minute strategy call can unlock real tax savings. Evolve owners get a $250-value session where we walk through tax deductions, tax strategy, entity structure and cash-flow impact—so you’re not guessing your way through STR tax planning.
- Great hospitality plus smart tax strategy builds long-term wealth. Evolve handles the guest experience; WCG handles the tax complexity. When both pieces work together, your rental becomes a true wealth-building venture instead of a part-time mystery with full-time headaches.
As part of this partnership, Evolve owners receive a complimentary 40-minute tax strategy session—a $250 value—focused on maximizing tax deductions, reducing tax drag, and improving after-tax cash flow. Yay!
Short-term rentals come with unique tax opportunities—and pitfalls—that most owners learn about the hard way. We help you understand how Evolve’s structure easily allows you to materially participate when using a property manager and correctly apply STR tax rules to deliver real-time losses that offset W-2 and 1099 income. Yay again!
Our goal is straightforward: remove confusion, eliminate bad internet tax myths (well, at least explain the myth), and give Evolve owners a clear roadmap for running their rentals like a tax-leveraging and wealth building business. Whether you’re buying your first property (congrats!), scaling to multiple units, or transitioning from long-term to short-term rentals, WCG provides sound tax reduction strategy for rental property owners (and beyond the STR loophole strategy). You focus on delivering great guest experiences; we focus on turning that effort into long-term investment strategy.
I Just Got A Rental, What Do I Do?
I just got a rental, what do I do? Purchasing a rental property is certainly challenging, but operating one to build wealth and find tax efficiency is equally challenging. This is our second book. Our first book, Taxpayer’s Comprehensive Guide to LLCs and S Corps, was first published in 2014 and was well-received by small business owners and tax professionals, so we thought a book on rental properties and real estate investments would be equally helpful. So, here we are with our second iteration, or the 2025 edition. We update it frequently throughout the year (last update was October 6, 2025).
Our rental property book starts with entity structures and moves into asset management such as acquisition, cost segregation, rental safe harbors, repairs versus improvements, accelerated depreciation, partial asset disposition, and 1031 like-kind exchange. From there we discuss various rental considerations like passive activity losses, short-term rental loophole, real estate professional status, and material participation including what time counts, and what time doesn’t count.
Finally, the good stuff! Rental property tax deductions such as travel, meals, automobiles, interest tracing, home office and common expenses. Fun!
It is available in paperback for $19.95 from Amazon and as an eBook for Kindle for 15.95. Our book is also available for purchase as a PDF from ClickBank for $12.95.
How To Purchase Our Rental Property Book
If you buy our 480-page book and think that we didn’t help you understand rental property tax laws, let us know. We never want you to feel like you wasted your money. If you are ready to add some insightful reading into your day, click on one of the preferred formats. Amazon is processed by Amazon, and the PDF is safely processed by ClickBank who will email you the PDF as an attachment.
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| $19.95 | $15.95 | $12.95 |
Chat With a Tax Pro
Taxes can be tricky. Chat with a WCG human now and get questions answered.
Frequently Asked Questions
Do I really get a free 40-minute tax strategy session as an Evolve owner?
Yes—Evolve owners get a $250-value strategy call with WCG. No pressure, no jargon, just real answers about your rental, deductions, and tax planning.
Can I still materially participate if Evolve handles guest communication and operations?
Absolutely. You can stay in charge of the big decisions, planning, and oversight while Evolve handles the day-to-day. The IRS cares about your involvement, not who sends the check-in instructions.
What services does Evolve actually handle — and what am I still responsible for?
Evolve handles listing creation (with professional photography), marketing across major platforms, dynamic pricing, bookings and guest communication, payment / reservation processing, and liability / damage protection or coordination with their vetted support network. This is some of the yucky stuff you’d rather have others do. You — the owner — remain responsible for furnishing your property, cleaning, restocking, maintenance, local permits/licensing, and filing tax returns making material participation much less of a hurdle. Divide, conquer, yet participate sort of thing.
What’s the benefit of qualifying for material participation on a short-term rental?
It can let certain losses offset W-2 and 1099 income provided you have an average guest stay of 7 days or less.
Is the “STR loophole” actually real?
Yes, it’s real—but it’s also misunderstood. Sure, the 7 day thing and the material participation seems straightforward, but there a ton of nuances like how to compute an average when converting to or from long-term, or which tasks or duties count as material participation, or what is “in-service date” and why you should care, among other things.
Does Evolve’s model help or hurt my tax position?
It generally helps. Their setup keeps you closely involved in the high-level decisions that count for material participation while freeing you from the stuff you don’t want to do anyway.
Should I get a cost segregation study on my rental?
Maybe. They can accelerate deductions through compressed depreciation, but you also want to time it correctly against spikes in income. You might also want to opt out of 5-year bonus (for example) while letting 7-year and 15-year fly! Tax planning is a must.
What if I’m brand-new to short-term rentals?
Perfect. Starting clean is easier than fixing bad habits later. We’ll help you set up the right structure, tracking, and expectations so your rental behaves like a real business from day one.
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