Dear Liz: When my husband was 65 years old, he was employed and covered by a high franchise health plan (HDHP) with a health savings account by his employer. Neither his employer nor our local social security office had concrete advice on how to register for Medicare, but after huge research, he finally delayed registration. Now I’m approaching 65 years. My husband is still working, and I am always covered by his health insurance, although both are in his name. Should I register for Medicare at the appropriate time or do I delay registration like him?
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Answer: The delay in registration in Medicare can cause penalties that can increase your bonuses for life. If you or a spouse still works for an employer with 20 or more employees, you can generally choose to keep the health insurance provided by the employer and to delay the Medicare request without being penalized. If you lose the coverage or the end of the job, you will have eight months to register before you are penalized.
The delay in your registration in Medicare also allows your husband to continue to make contributions on your behalf to his health savings account. In 2025, the HSA contribution limit was $ 4,300 for self-monetary coverage and $ 8,550 for family coverage, plus a remedial contribution of $ 1,000 for account holders of 55 and over. Once you have registered in Medicare, HSA contributions are no longer allowed.
Medicare himself suggests contacting the employer’s benefits service to confirm that you are properly covered and that you can delay your request. Hopefully your employer’s human resources service has now accelerated this important subject.
Dear Liz: We read your recent column on capital gains and sales of houses. Our understanding is that if you sell and then buy a property of equal or higher value in the 180-day window, the basis for tax purposes is the purchase price, the more the exemption of $ 500,000, the more property improvements, the less depreciation, whatever this number, then the above profit which must be reinvested or is subject to capital gains. We talked about it to our CPA and he referred to a site specializing in exchanges 1031.
Answer: You have gathered two different sets of tax laws.
Only the sale of your main residence will qualify for the exemption from home sales, which for a married couple can exempt up to $ 500,000 from home sales profits from taxation. You must have owned and live at home at least two of the previous five years.
Meanwhile, 1031 exchanges allow you to postpone capital gains on investment buildings, such as commercial or rental real estate, as long as you buy a similar property within 180 days (and follow a lot of other rules). The replacement property should not be more expensive, but if it is cheaper or has a smaller mortgage than the property you sell, you may have taxes on capital gains on difference.
