In another question, I mentioned that O-protonation of an enolate followed by tautomerization may lead to increased amounts of the thermodynamic product over the kinetic product (when those are different species). The idea that the oxygen is likely protonated first has been discussed previously...

The accepted answer doesn't answer the question but merely rejects it. The reason is due to the steric repulsion of the methyl group on oxygen's lone pair. This makes it less donating and hence less activating to the reactant. The other answer says that it should be considered almost equal ...