Dear Liz: When my husband approached 65, his employer hired a High Deduction Health Care Plan (HDHP) and his employer provided a health savings account. Neither his employer nor our local Social Security Office have specific advice on how to continue enrolling in Medicare, but after a huge study, he eventually delayed enrollment. Now I am close to 65 years old. My husband is still working and I am still covered by his health insurance despite being in his name. Am I joining Medicare at the right time or do I delay enrollment like him?

answer: Delaying Medicare admission can result in a fine, thereby increasing your lifetime premium. However, if you or your spouse is still working for an employer with 20 or 20 employees, you can often choose to retain the health insurance provided by your employer and delay applying for Medicare without penalty. If you lose coverage or employment purposes, you will have eight months to register before being punished.

Delaying your Medicare enrollment also allows your husband to continue to donate on behalf of your health savings account. In 2025, the HSA contribution limit is $4,300, the household coverage is $8,550, and the $1,000 catch-up contribution from account holders 55 and older. Once you participate in Medicare, HSA donations are no longer allowed.

Medicare itself recommends contacting the employer’s welfare department to confirm that you have covered appropriately and may delay your application. Hopefully, now your employer HR has begun to accelerate this important topic.

Dear Liz: We read your recent column on capital gains and home sales. Our understanding is that if you purchase property of equal or higher value within a 180-day window, the tax purpose is based on the purchase price, plus a $500,000 exemption, plus improvements to the property, minus depreciation of depreciation, regardless of the depreciation brought by that number, then the profits that have to be repaid, or reinvest or suffered from capital taxes. We discussed this with the CPA, who referred us to a website specializing in 1031 communication.

answer: You smash two different sets of tax laws together.

Only selling your primary residence is eligible for a home sale waiver, which for married couples, is exempt from $500,000 in home sale profits. You must own and have owned and resided at least two people over the past five years.

Meanwhile, as long as you purchase similar properties within 180 days (and comply with other rules), you can postpone capital gains on investment properties (such as commercial or leased real estate). Alternative properties don't have to be more expensive, but if it's cheaper or the mortgage is smaller than the property you're selling, you can owe the difference capital gains tax.