Tax is often about timing. Timing issues are those where the taxpayer defers the requirement to pay taxes to a later date. Preferably a later date that is many, many years in the future. The hope is that the taxpayer can retain the amounts that would have been paid in tax today and use the…
Category: Federal Income Tax
Federal Income Tax
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Tax Court Clarifies Employee Tool Plans
Prior to the Tax Cuts and Jobs Act (“TCJA”) of 2018, it was common for employers to simply pay employees more and leave it to the employees to deduct their employee business expenses on their personal income tax returns. The TCJA limited the employee’s ability to deduct employee business expenses. Many employers responded by adopting…
The Late Mark-to-Market Election
Those who trade stocks can take advantage of the mark-to-market election to convert capital losses into ordinary losses. This election is only available to “traders.” There are often questions as to when a taxpayers trading activities are sufficient to warrant being treated as a “trader” for tax purposes. By the time the taxpayer discovers that…
Tax Loss Planning: The At-Risk Rules
Are you purchasing a business or real estate that involves financing a business or investment that is likely to produce tax losses in the future? Or have you already made the purchase? If so, there may be ways to ensure that you can take the loss in the future. To do so, you have to…
Can “Business Synergies” be an Asset that Increases a Tax Loss?
The tax consequence of a transaction often depends on how one characterizes or describes the transaction. Business synergies are often cited as the rationale for merger and acquisition deals. In a M&A deal, are “business synergies” a separate asset for tax purposes? Can you list “business synergies” as a separate asset and then take a…
Big Tax Savings With ESOP, But Requires Work
An employee stock ownership plan (ESOP) can produce significant income tax savings. This tax savings isn’t exactly free. One has to keep up with the ESOP and the relevant rules to ensure that the tax savings are achieved. This compliance work is required and failure to comply can be costly. The recent Ed Thielking v.…
Tax Planning for the Start-up Limitation Rules
Our tax laws include start-up rules that limit the ability to deduct certain business and investment expenses. For business owners and investors with other sources of income, this can result in funds being sent to the IRS to pay taxes at a time when the capital is needed to fund the business or investment growth.…
Tax on Payment for Being Born With Medical Condition
We can do some amazing things given the state of our science and technology. These advances lead to some interesting tax questions. The IRS recently addressed such a question in PLR 201950004. It considers whether damages paid by a fertility clinic for failing to perform a genetic test are excluded from the recipient’s income as…
Installment Sale Treatment for Mobile Home Trailers
If you buy, subdivide and sell real estate, can you seller-finance the sales and report the gain using the installment sale method? The installment sale method can defer paying tax on the sales by allowing you to recognize the gain in later tax years. As the court in the Joyner Family Limited Partnership v. Commissioner,…
Bad Debt Tax Deduction for Guarantee Payment?
When an individual or company guarantees a loan for a third party, they are essentially agreeing to assume responsibility for the debt if the borrower defaults on their payments. In some cases, the guarantor may be required to make payments to the lender on behalf of the borrower. But what happens when the guarantor has…