First, a technical clarification - the HSA belongs to either you or your spouse (in fact, you could each have an HSA). There is no such thing as a Family HSA. It's the HDHP policy that can give you Family coverage.
There are two basic types of transactions for your HSA: contributions and distributions. The contributions done through your employer are entered on the W-2 in box 12 with a code of W. All such contributions through the year are lumped together.
If you made "personal" contributions (i.e., NOT through the employer but directly to the HSA), then you lump all of these together and make one entry on the screen entitled "Let's enter [name]' HSA contributions".
The distributions (amount you paid for qualified medical expenses) are similar in that they are lumped together. You should have received a form 1099-SA from the HSA custodian containing all the distributions for the year. Note that there are reasons that you might receive more than one 1099-SA, but that would be only two such forms.
If you have not received your 1099-SA for all your medical expenses, then please go to your HSA custodian's website and see if the form is available online (it often is). Otherwise, just ask a customer service rep.
As you can see, there is no need (or way) to itemize all your transactions from your HSA.
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