@RedBaron96 - 

While I could do an entire series of classes and sermons on what Heaven is like and what it is, I will just stick to your questions!

Using all of scripture as a basis (good place to start, eh?):
I do not think that those whom have gone before us can see what is happening "down here."  Nowhere in scripture does it mention people in Heaven talking about or getting involved with the happenings of Earth.  The closest it comes is in Revelation 6:10 when those killed for the Word of God exclaim "How long, Sovereign Lord, holy and true, until you judge the inhabitants of the earth and avenge our blood?" (NIV) and God tells them to wait until their number is complete.  There is no indication that they are following what is going on.  (I also know I could be wrong)

When in Hebrews 12:1 it mentions the witnesses, it is merely a metaphor, saying that all of these others have done what we need to do, set the example if you will.  It is like in a courtroom when someone points out "Your DNA is a witness against you!"

It is the Father, through His Spirit, that is watching us continually.  Which leads me to the other question:

I do think angels are constantly watching over us!  I like to think of it as a shift thing:  They take shifts watching us!

I could be wrong on some of this, sure.  For the most part, I am confident in this.  I do think that those who have died understand some of the things going on throughout history, but they are not really "watching" us.

@DanDantheGodman -