Yes, the receipt from the charity and your written record of what was donated should meet the requirements for Contemporaneous written acknowledgment (CWA).
The CWA doesn't have to be a letter, but it must include the charity's name, address, date, and donation location. You can provide the list of items and description of condition, which must be in good used condition.
The regulations state there must be sufficient detail to determine fair market value.
There's no advantage to donating more often because all of your donations of similar items during the year are grouped together to determine the documentation needed.
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