Tax Q&A: Short-Term Rentals, 1099 Confusion, Entity Conversions, and Creative Tax Strategies
Tax Q&A: Short-Term Rentals, 1099 Confusion, Entity Conversions, and Creative Tax Strategies  
Podcast: Small Business Tax Savings Podcast
Published On: Wed Feb 12 2025
Description: Send us a textHave you ever considered how advanced tax strategies, from customized retirement contributions to optimizing home office deductions, might lower your overall tax burden? In this Q&A episode, host Mike Jesowshek answers listener questions on various tax topics. He covers issues ranging from retirement planning strategies, such as after‑tax contributions and Roth conversions in a solo 401(k), to the proper methods for paying oneself as a sole proprietor versus an S corporation. Mike also explains home office deductions, board meeting expenses, handling duplicate tax forms, and business entity conversions. [00:00 -  05:02] Retirement Contributions and Solo 401(k) OptionsMike discusses using after‑tax contributions and a Roth conversion in a solo 401(k) for high‑income earners.New members receive immediate access to a comprehensive suite of tax-saving tools and consultations.[05:02 - 10:42] Owner Draws, Home Office Deductions, and Board Meeting ExpensesMike explains how to oneself as a sole proprietor using owner draws versus payroll for S corporations.Understand that taking money out of a business as an owner draws does not reduce taxable profit.Ensure that business spaces are used exclusively for business, and document meetings carefully when using home space.[10:42 -  15:32] Hiring Family Members, Deducting Mileage Expenses, and Entity ConversionMike discusses claiming mileage expenses when an employee uses a personal vehicle for business.Recognize that converting a C corporation back to an LLC may trigger taxable events; professional consultation is advised.[15:32 - 20:17] Handling Duplicate 1099 Forms and Short-Term Rental DeductionsWork with the issuer to correct mistakes or offset the extra reporting with a matching expense entry.Understand the timing of deductions and whether expenses need to be capitalized based on service start dates.[20:17 - 27:20] S Corporation and Subsidiary Structures; Home Office with Additional FacilityMike details the benefits of an S corporation holding company structure for multiple LLCs and addresses home office deductions when using a separate facility.Proper structuring can consolidate profit and loss reporting, and the administrative office rule allows a home office deduction even when an additional business location exists.Direct Quotes:"If you are helping out family members, and those family members can also do some work for your business, why not get a business deduction for that help that you want to do anyways?" - Mike Jesowshek, CPACheck out this episode’s blog post! Visit https://www.taxsavingspodcast.com/blog/tax-q-a-short-term-rentals-1099-confusion-entity-conversions-and-creative-tax-strategies Click here to book a demo call or you can visit https://taxelm.com/demo/ ______Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings PodcastJoin TaxElm: https://taxelm.com/-------Podcast Website: https://www.TaxSavingsPodcast.comFacebook Group: https://www.facebook.com/groups/taxsavings/YouTube: www.