1. EachPod

40. STR Tax Hacks: Depreciation, Deductions & Keeping It Legal

Author
Brittany Wenninger
Published
Tue 09 Sep 2025
Episode Link
https://brittany-wenninger.mykajabi.com/podcasts/how-to-start-an-airbnb/episodes/2149083530

How to Redeem the Offer


Text ROADMAP to 608-492-0260 (tell them you came from The Airbnb Roadmap) to get 1 free month off a 3-month accounting subscription and the STR Accounting & Tax Cheat Sheet.


 


Airbnb Roadmap Accelerator Course



  • Want to learn how to launch an Airbnb?: Every dollar counts when it comes to investing. Save $50 with the Promo-code: 5STARPODCAST



 


In this episode, I sit down with my bestie, Kari—owner of BOOKED (Accounting & Tax), to demystify bookkeeping and taxes for first-time short-term rental investors. We get real about what matters on day one (hint: separate bank account!), when you actually need QuickBooks, how to track receipts without losing your mind, and the biggest tax levers for STRs (material participation, real estate professional status, and bonus depreciation). Kari also shares transparent pricing, an exclusive promo code: ROADMAP, and a free cheat sheet that recaps the episode. If you’ve ever wondered, “What should I be tracking, and how do I not overpay at tax time?”, this one’s your playbook.


Key Takeaways



  • Separate your money from day one. Open a dedicated business bank account for your STR. Keep every dollar in/out separate from personal spending.


  • You don’t have to start with software. A simple spreadsheet + a folder of receipts works for your first property. Scale into QuickBooks Online when transactions grow (BOOKED passes along firm-level discounts).


  • Save every receipt. Little expenses add up—and they matter during month-end, tax time, and if you’re ever audited.


  • Know where you land: Schedule E vs Schedule C. Most STRs file on Schedule E (rental). If you provide hotel-like services (meals, concierge during stays), that can push you toward Schedule C (business) with self-employment tax.


  • Material participation can be huge. If you actively manage and meet IRS tests, your STR losses (including depreciation) may offset other income.


  • Real Estate Professional Status (REPS). If you qualify, you may be able to apply STR losses against W-2/active income, game-changer for some hosts.


  • Bonus depreciation is back in a meaningful way. Eligible furnishings/appliances can be expensed in the year placed in service, talk to your accountant about what qualifies.


  • Mileage is money. Track business drives to/from your property. The QuickBooks mobile app can automate this.


  • Personal use complicates taxes. The more you use the property for yourself, the more expense allocations you’ll have to make, be intentional.


  • Cash flow is seasonal. Don’t blow your peak-season profits, budget for the quiet months.



Why Listen to This Episode?


Because you want clean books, maximum deductions, and fewer headaches. You’ll learn exactly what to track, when to outsource, and how to avoid the “I’ll fix it at tax time” premium. Kari’s firm is built for “baby businesses” and first-time hosts, fast replies, transparent pricing, and real-world guidance.


Mentioned in the Episode




    • BOOKED (Accounting & Tax) — full-service accounting, payroll, taxes, entity setup, ongoing support; transparent pricing and fast response times


      • Promo code: ROADMAP — text this keyword for 1 free month off a 3-month accounting subscription (month-to-month; no long-term lock-in)




 



  • Kari Richard


 



Let’s Connect


Thinking about bookkeeping and taxes for your short-term rental? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.


Work With Me



  • Buy/Sell/Invest in Wisconsin: Front Porch Realty (powered by Real Broker LLC) ,  I help investors and homeowners win smart.


  • Airbnb Roadmap Accelerator (self-paced): Learn how to find, launch, and manage your first STR with confidence, systems, templates, and step-by-step guidance.


  • 1:1 Guidance: Need strategy on a deal, setup, or regulations? Ask about consults and mentorship options.



Chapters



  • 00:00 – Cold open, why we’re keeping the bloopers 😄


  • 02:06 – Meet Kari + why BOOKED serves “baby businesses” and first-time hosts


  • 07:32 – The real first step: separating finances (and why receipts matter)


  • 10:50 – Entity basics & getting set up; simple spreadsheet vs software


  • 15:23 – Tools: QuickBooks Online, discounts, and what makes reconciliations faster


  • 24:29 – STR tax levers overview: participation, REPS, depreciation


  • 27:05 – Schedule E vs Schedule C—what changes and when


  • 30:01 – Bonus depreciation this year: what hosts should ask their accountant


  • 32:21 – Material participation & REPS: tracking hours and what counts


  • 34:09 – Deductions rundown: mortgage interest, taxes, insurance, HOA, utilities, cleaning, travel, mileage


  • 36:24 – Pitfalls: personal use, mixed expenses, misclassification, seasonal cash flow


  • 43:57 – Tax planning wins: when to buy, when to expense, how to think ahead


  • 48:51 – Transparent pricing: $25/mo support plan, $89/mo popular package, month-to-month


  • 54:54 – Promo code ROADMAP + free STR accounting cheat sheet


  • 56:19 – Wrap and where to get help fast



Subscribe and Share


If this episode helped you feel more confident about your numbers, follow/subscribe, drop a 5-star review, and share it with a fellow host who needs an accounting upgrade. Your shares help more first-time investors find this show. 💛


How to Redeem the Offer


Text ROADMAP to 608-492-0260 (tell them you came from The Airbnb Roadmap) to get 1 free month off a 3-month accounting subscription and the STR Accounting & Tax Cheat Sheet.

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