Just throwing this question up because 1 it interests me and 2 because i feel like after playing guitar for some time this is something that always comes up, wanting to just listen to something on the radio or whatever, and be able to imitate it and/or play with it.

If you dont mind adding a bit of backround with the poll answer id appreciate it. How long had you been playing when you learned, how long did it take to get comfortable doing it, Does the difficulty of the song really impact it, does it have any connection with say improving over some radio song, what helped you get there, etc?

I have been pursuing this very thing, and ive gotten plenty of help, but i can see that it takes awhile, i have trouble figuring out things like the first 3-4 notes to kumbaya, and thrown some chords in there as well, and im practically screwed Just looking for thoughts/ideas/reassurance that might be helpful to me

Kindof sometimes occasionally

Yes, Very well (piano)
though some songs are harder than some because of unusual chords, but the melody is something easily memorizable.
If you have troubles hearing what chords are under a melody you can learn them all ( 7th, 9th are the most used) but some are a bit more complex then that but it's a lot about practise.

Pretty much this.

Assuming you have a good musical background, it's pretty easy to figure out a song (especially since what you hear on the radio is the same simple shit all the time)