Why are the secondary alpha hydrogens more acidic than primary alpha hydrogens (keto-enol tautomerization)?
You're actually asking two questions. There is both kinetic and thermodynamic acidity. There are times when performing deprotonation at low temperature will yield the kinetically favored conjugate base, i.e., the proton that is most exposed. If you increase the temperature of this intermediate, you can get to the point where proton transfers happen in reaction vessel to create the more stable thermodynamically favored conjugate base. Usually, this is the more substituted one.