1. There is no such thing as an individual FSA. All FSAs cover both spouses. So in January 2026 (or whenever) neither one of you should sign up for the FSA.
2. Don't sign up in August for anything except HDHP coverage.
3. Your wife can open her own HSA the moment she is eligible to (i.e., has HDHP coverage and no conflicting coverage). NOTE: she SHOULD open her own HSA as soon as she is eligible. This is because there is a $1,000 increase in the HSA contribution limit for those who are 55+, but only the person who owns the HSA can contribute this amount. Therefore, after you are on Medicare, she HAS to have her own HSA in order to be able to utilize this benefit.
4. There is no such thing as a Family HSA. It's the HDHP policy that is Family or Self-only. An HSA is similar to an IRA in that it is owned by one taxpayer.
5. Given what I have just said, this question doesn't make sense. I have already told you what the Medicare up to 6 month look back means.
6. Are you going to start Social Security at some point (like at age 70 when benefits stop increasing)? When you start SS, then the SSA will sign you up for Medicare Part A whether you like it or not. This will be the end of you being able to contribute to your HSA.
7. As I noted above, it is the HDHP that is Family, not the HSA. If your spouse has any dependents, then your spouse can get a Family HDHP policy, without regard to you.
NOTE, even after you go on Medicare, you can still pay for qualified medical expenses for either one of you, it's just that you can't contribute to the HSA any longer.
P.S. I am a TurboTax seasonal employee and an Enrolled Agent...I have answered perhaps 9,000 HSA questions in the last 9 years. Thank you for being thoughtful.
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