"if She has Family and He has Self " - that isn't the terminology. If one spouse has Family HDHP coverage, then they both do, in terms of calculating the annual HSA contribution limit, no matter what their individual policies may say.
The $1,000 "bonus" is not a function of Family or Self but belongs to the HSA owned by someone who is 55+ and covered by some (any) sort of HDHP without conflicting coverage.
"So it's really $9100, if you do it right....." No, as Opus points out, if you have 2 HSAs in the mix, the max is in toto $8,850.
Having said that, I admit I was fixated on one HSA. Why? Because of "How much can my wife and I can contribute to an HSA for 2020?" Being a literal man, I thought in terms of one HSA.
But, even worse, I took this to mean that they had no HSA for 2020 at all. They might not for all I know and are just asking how to create and populate an HSA for 2020.
I presumed that if they had an HSA that he have it. I had the advantage of answering the identical question from Jeremy but for 2021, which was considerably easier since his spouse was not eligible to make any contributions at all in 2021.
So I carried over that "one HSA" thought to this question, which I answered subsequent to the 2021 question.
To your collective calculations, we agree that the maximum that he can contribute to his HSA is $8,100. Then as you two point out, if you add another HSA to the mix (and I still don't know if she has one or not, but she could create one retroactive to 2020), the maximum she could contribute to her HSA in this case is $750 (9 months of the $1,000 bonus).
This brings us to Opus's $8,850, although NCperson would have arrived at the same number had the calculation of "$1000 * .75??????? " been completed.
However, please note that in this case, it is absolutely irrelevant if the spouse had Self-only coverage from a different HDHP policy or was under his Family coverage. The moment that he had the Family coverage, they shared the $7,100 for the year.
It is true that you could not contribute more than $5,325 + $750 to her HSA, which would leave him $1,775 + $1,000 for his HSA, so $6,075 for her and $2,775 for him, which again adds up to the $8,850.
No matter how you allocate the $7,100 Family coverage, they must contribute at least $1,000 to his HSA and $750 to her HSA.
Thanks for bringing up the thought of a second HSA (if Jeremy was even thinking of it 😉 ) - not having that would have left $750 on the table.
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