I doubt enolizable protons have anything to do with it. Most reagents used (IE hydroxide) are not strong enough bases to come anywhere close to quantitatively deprotonating that alpha carbon, so formation of enolate shouldn't factor into electrophilicity much.
I'd worry much more about steric effects with the alpha substitution, IE the trimethyl ester is less reactive than the dimethyl ester. That's because the electron donating ability of a Carbon-Carbon bond is about the same as the electron donating ability of a carbon-hydrogen bond, so they are roughly electronically equivalent.
In short, my best guess is rank them first using electronic effects (IE chloride most reactive, ester in middle, then amide), then use steric effects to rank within those categories.
I am less sure about the methylation at nitrogen, though.