Does a retail store's point-of-sale and inventory system data actually transfer with the sale?

Not automatically, and this is worth confirming early rather than assuming the software and its data simply come with the store. Point-of-sale and inventory management systems are often licensed from a third-party vendor rather than owned outright by the retailer, which means the licence itself, not just the historical data sitting inside it, needs to be addressed in the sale — some licences are transferable with the vendor's consent, others are personal to the original licensee and require the buyer to set up its own account or subscription entirely.

The underlying data — sales history, inventory records, supplier costs, customer purchase history — is a separate question from the software licence. In a share sale, since the same corporation continues, both the licence (subject to the vendor's own terms) and the data generally continue uninterrupted. In an asset sale, the purchase agreement needs to specifically address export or transfer of the historical data, since a new buyer entity typically can't simply inherit the seller's existing vendor account.

Confirming directly with the software vendor what's transferable, and building data export and account transition into the closing timeline, avoids losing valuable historical sales and inventory data right when a new owner needs it most.