RAW neither a hand crossbow nor a pistol can be fired more than once along side of a shield, even with repeating shot or XBE. Repeating shot and XBE eliminate the loading property but not the ammunition property. The ammunition property requires a free hand to load the weapon.
Repeating Shot enables firing alongside a shield because it also overrides the ammunition property with the following line:
If you load no ammunition in the weapon, it produces its own, automatically creating one piece of magic ammunition when you make a ranged attack with it. The ammunition created by the weapon vanishes the instant after it hits or misses a target.
You only need a free hand to load in ammunition, but if you don't do that it does it for you when you fire, so need for a free hand at all.
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Former D&D Beyond Customer of six years: With the axing of piecemeal purchasing, lack of meaningful development, and toxic moderation the site isn't worth paying for anymore. I remain a free user only until my groups are done migrating from DDB, and if necessary D&D, after which I'm done. There are better systems owned by better companies out there.
I have unsubscribed from all topics and will not reply to messages. My homebrew is now 100% unsupported.