My take on the reason is that logos become more abstract in proportion as the business expands and therefore generalizes its products and services.

Amazon started out at something very specific, an online bookstore, but evolved to become just Store in the abstract and universal sense. The old logo becomes a fetter on the brand and has to give way for a more abstract logo that can accommodate all of the different things that the brand wants to do.

Cracker Barrel, as a simple restaurant chain, is limited as a brand. Cracker Barrel as an experience, well that can be anything. They can pivot into anything that vaguely instills the same nostalgic feeling, and if the groundwork has already been done, then consumers won’t be confused or alienated when Cracker Barrel starts selling cars or something. So more and more, Cracker Barrel isn’t a particular thing, it’s an idea. The capitalist tendency toward monopoly necessitates this result, as the very point of branding is to convince you that two identical commodities are in fact distinct and not interchangeable.