The power and toughness boosts apply over Humility's setting of the base p/t. As for abilities, wether they are removed is indeed determined by timestamp. The ability-granting effect will work if it has a later timestamp than Humility. For an emblem, the timestamp is the emblem's creation. For an enchantment like Always Watching, it's when it entered the battlefield.
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I'm a former judge (lapsed), who keeps up to date on rules and policy. Keep in mind that judges' answers aren't necessarily more valid than those of people who aren't judges; what matters is we can quote the rules to back up our answers. When in doubt, ask for such quotes.
Continuous effects that alter characteristics are applied in a series of layers. The buffs will happen regardless of time stamps, because power/toughness setting effects (like Humility) are applied in an earlier sublayer than power/toughness modifying effects. The additional abilities, though, are applied in the same layer as ability removing effects, so time stamps matter. Any ability granting effect with a later time stamp than the ability removing effect will result in the creatures having that ability. Emblems are no different in that regard than a permanent like AW.
To my understanding, my creatures will get vigilance if I play Always Watching after Humilty? Or does it happen no matter the order?
Is that true for Emblems? Such as that Elspeth, Sun's Champion? Do I have to play the emblem after so they can get the ability buffs?
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