Claisen rearrangement in substituted ring
Another great example of how it's important to look at actual evidence. There have been various studies on Claisen rearrangement selectivity, here's a combined experimental/theoretical one on meta-substituted ethers specifically: Gozzo, F. C.; Fernandes, S. A.; Rodrigues, D. C.; Eberlin, M. N.; Marsaioli, A. J. Regioselectivity in Aromatic Claisen Rearrangements. J. Org. Chem. 2003, 68 (14), 5493–5499. DOI: 10.1021/jo026385g.

An important screenshot is shown here:



Based on this article at least, it turns out that for your specific reaction, it's likely that the regioisomers would be formed in equal amounts. (See allyl aryl ether 1). We further see that sterics are not as significant of a consideration as electronics; allyl aryl ether 6 actually prefers the "more sterically hindered" product 14 to 1.

The article concludes that "the preferred conformation of the reactants ... with no exception, was found to lead to the major isomeric product.... The regioselectivity for the Claisen rearrangement of meta-substituted allyl aryl ethers is mainly influenced, as expected, by the electronic effects of the meta substituent, which governs the relative stability of conformers, transition states, and intermediate to final products.