I don't see what the point is in the search and insert mode.

Its point is to allow you to call up one song and having it play without affecting or getting rid of all the other stuff you're currently listening to.

Example: I'm listening to a long playlist of background music while I'm working. Then I get a hankering to listen to a particular song. Maybe that song is in the playlist, maybe it's not. But I can search it up by title and it will play as the next tune, without interrupting the flow of the music that's playing right now. The song fits nicely into the list as if it were meant to be there all along, with the songs flowing smoothly along one into the other.

In fact, I don't see how that's much different from what you want to do, except that in this case, it has the advantage of not interrupting the flow of music, and also has the advantage of being able to look up songs that aren't in the current playlist. To do what you want to do (jump immediately to the seached song in the playlist) has pretty much the same audible result as a search/insert followed by pressing the next track button.

You still haven't answered my question, though, which is: Why is it critical for you to jump forward in the playlist? I would understand if playlist position was important when you're listening to an album sequentially, but you specifically said that you didn't rip all your albums and you only have your favorite songs on the player. So listening to sequential albums doesn't seem to be what you're after. So what is it then?

Why would you have the player take the song you said you wanted it to play and put it in front of the current song when you could be able to just play it now?

You can just play it now, that's one of the options ("replace"). You can also insert it, and play it now by pressing one button.

Although you keep saying "in front of", and I hope that's just a difference in chosen semantics. To me, "in front of" would mean before the current track. What "Insert" actually does is put it after the current track so that it comes up as the next song. If you really think that "Insert" puts it before the current track, then I understand why you would think that's useless. Good thing it doesn't work that way.

If you wanted it played directly after the current song then they should call it enqueing or something right??

Yes, enqueue is also one of the options. The difference between Enqueue and Insert is subtle, and is described in the FAQ.