#569 Tax Lawyer QnA: Strategies The Rich Use to Avoid Paying Taxes

Main Street Business

In this episode of the Main Street Business Podcast, Mark J. Kohler and Mat Sorensen dive into listener questions about tax and business planning. From maximizing deductions on rental properties to creative financing strategies for commercial real estate and smart ways to restructure an LLC, they address the biggest tax and business concerns entrepreneurs and investors face.

Here are some of the highlights:

• Mark explains the benefits of short-term rentals, including accelerated depreciation and cash flow.
• Mark & Mat provide a detailed explanation of how short-term rentals can be grouped under the 469-4 election and the importance of material participation.
• The importance of understanding the long-term play when dealing with short-term rentals.
• A breakdown of various creative solutions like subleasing and seller financing to mitigate the financial burden.
• The potential of seller financing and the benefits of carrying the paper for a premium.
• The possibility of condominium conversion as a unique solution to increase a property's value.
• Mark & Mat discuss the potential pitfalls of borrowing against equity and the importance of generating income to pay debt service.
• The importance of keeping assets that have great cash flow or appreciation and the potential for 1031 exchanges.

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Chapters

1. Introduction and Open Forum Setup (00:00:00)

2. Short-Term Rental Grouping Election Strategies (00:04:12)

3. Problem Commercial Property Solutions (00:10:28)

4. Buy, Borrow, Die Strategy Analysis (00:22:41)

5. BOI Reporting Requirements Update (00:30:46)

6. Family LLC and Board Meetings (00:34:10)

7. Land Trust vs LLC Privacy Structures (00:41:01)

8. New Business Structure Considerations (00:49:15)