Clouds or Colt? Righteous or Wicked?

Take a look at these prophesies:

Zechariah 9:9

Rejoice greatly, O daughter of Zion; shout, O daughter of Jerusalem: behold, thy King cometh unto thee: he [is] just, and having salvation; lowly, and riding upon an ass, and upon a colt the foal of an ass.

 and

Daniel 7:13

I saw in the night visions, and, behold, [one] like the Son of man came with the clouds of heaven, and came to the Ancient of days, and they brought him near before him

So, what are we to think if we were studying the Prophets before that great Passover festival almost 2, 000 years ago?  What would we think if we were there then, seeing this One that we expect to be The One riding into Jerusalem on a colt?  What are we to think today if we are among those who don’t recognize Yeshua as the Coming One?  What’s the deal?  How is Messiah supposed to come???

I learned a bit ago that:

If Jerusalem is wicked, Messiah will come riding on the foal of an ass but if Jerusalem is righteous, Messiah will come on the clouds of Heaven.

If we didn’t have hindsight, what would we think?  Even if we accepted the Two Messiah concept, Messiah son of Joseph and Messiah son of David, what would we think?  Would anyone hold too tightly to one Messiah with two comings or would we more likely consider there being two different Messiahs?  

Knowing what most of my readers believe, that Yeshua son of Joseph yet Son of HaShem is the promised Messiah, what do we think of these verses and the interpretation concerning Jerusalem and it’s state of wickedness or righteousness?  How is it that Jerusalem may be considered righteous enough for Messiah to return?  Any ideas?  I’ve got several, myself…