"I turn 65 on Nov 30, 2026"
The problem with this planning is that the Social Security Administration makes it difficult to know when you are actually starting on Social Security.
Medicare starts either on the first of your 65th birthday month, or on the 1st of the previous month if your birthday is on the first of the month, or if you sign up within 6 months of turning 65, the start date is set back to the 1st of your birthday month, or once you are beyond 6 months from your 65th birthday, the most backdating is 6 months.
Please see this Medicare webpage to see if that makes more sense.
But I recently heard of a user here who applied for Medicare, and the SSA dated the coverage starting on the date of application, not the date that he/she requested that the coverage start.
Having said all that, consider this:
Whether or not you have Family coverage is a function of a taxpayer (whichever one of you) having coverage that is shared with at least one other person. The "other person" does not have to be eligible to contribute to an HSA. Thus, if the HDHP plan was in your spouse's name, even though you went on Medicare, your spouse could continue Family coverage, as long as you were also listed on the policy.
In the two years in which one of you will be eligible to contribute to an HSA, you will have to evaluate the additional cost of the Family plan versus the HSA contribution benefit.
In such an environment, in the year that you turn 65, the only thing that gets really limited is the amount of the $1,000 "bonus" that you can contribute to your HSA. If you have arranged for the Family coverage to be in your spouse's name (i.e., your spouse's policy), then the Family coverage will not be limited at all in that year if your spouse is the primary recipient of HSA contributions.
But if your Medicare starts on November 1, 2026, you would get to contribute 10/12 * $1,000 to your HSA, your spouse could still contribute the full $1,000 to your spouse's HSA, and the $7,100 (or whatever it will be), will still be available to divide between you and your spouse, so long as you don't get more than 10/12s of it into your own HSA.
Just bear in mind the link I gave you above in case the SSA ever changes its policy on when it starts Medicare.
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