1. You do not automatically lose HDHP coverage when you turn 65 - many people think that but it's not true - you only lose HDHP coverage when you actually sign up for Medicare. You can be 67, not on Medicare, and on an HDHP and still contribute to your HSA.
2. The catch-up to the contribution limit is for the owner of the HSA. The HSA belongs to an individual, no matter that both spouse can usually contribute to it and both spouse's expenses can be paid out of it. So if the HSA belongs to you, you can contribute up to $8,000 for 2019 if you have Family coverage. If your spouse also has an HSA and is 55+, then you two can contribute another $1,000 to her HSA, for a total of $9,000 - but you have to put at least $1,000 in each HSA.
So did you and your wife have separate HSAs?
3. TurboTax assumes that you are going to use the last-month and calculates accordingly. It would be nice if there were an option to turn it off, but to be honest, most taxpayers would have no idea what the last-month rule was.
4. When you apply for Medicare, the SSA sometime back dates the application by 6 months, which means that you would lose your HDHP coverage in 2019 (depending on when you applied for it). So have you applied for it? Did they backdate?
5. "am I correct that my max HSA contribution for 2019 should have been $6666.67," - as far as TurboTax and your 2019 return is concerned, your HSA contribution limit is $8,000. You don't need to change that. TurboTax won't report an excess contribution this year, if you change the months of coverage back to what it should be.
6. Then next year, when you answer "What type of HDHP coverage did [name] have on December 1, 2019?", you will answer "Family", and TurboTax will detect a lapse in coverage because you did not indicate that you were covered all year in 2020.
Then you will be taken through some screens whose job it is is to determine how much you should have contributed without the last-month rule and calculate what to do. The "excess" will be added back to Other Income and any penalty assessed.
7. Yes, you are right that the max annual contribution in 2019 would be $6,666.67 without the last-month rule. I imagine that the $1 is from a rounding error (TurboTax tends to round numbers immediately).
Your puzzlement on why the $1 instead of $833 may be because how you reported that other $1,000. Was this on your W-2 or what?
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