Claisen rearrangement in substituted ring This is an example of Claisen rearrangement, property of allyl vinyl/phenyl ethers.

I believe that the allylic migration should take place to the position ortho to both $\ce{-CH3}$ and $-\ce{OR}$ because: 


There's more electron density there due to the presence of electron donating group $\ce{-CH3}$ 


and I read this in March under Claissen rearrangement: 


  Since the Claisen rearrangement doen't involve ions, it shouldn't greatly depend on the presence or absence of substituent groups on the ring. This is the case. Electron donating groups increase the rate and electron withdrawing groups decrease it, but the effect is small. 


So I expect the product to be 2-[(2​E)-but-2-en-1-yl]-3-methylphenol: 

 

However my teacher made us write the product to be 2-[(2​Z)-but-2-en-1-yl]-5-methylphenol: 



His rationalisation was that the carbanion like species attacking the allyl group is more stable at the place away from methyl group. 

But my question is that if this reaction is single step, followed by tautomerism why should it even depend on the carbanion like species which isn't even formed.
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.