Playlists not syncing

Update, I'm not sure what was wrong with one particular song, but removing its download and downloading again fixed the issue of having to constantly authorize the computer in order to play that song. I've also taken the time to remove a bunch of older devices from my account, so that only my current laptop and phone are authorized. I'm still having two issues when it comes to playlists though:

1. Purchased content isn't automatically being downloaded to my computer, instead it remains in iCloud until I manually download it. When I do do that, it does not get added to the purchased playlist on my phone's device sidebar in iTunes, nor the main iTunes playlist, but it still appears in that list when viewing from the phone itself.
2. When viewing my phone's purchased playlist through iTunes, several songs are shown as copying, despite a sync not being in progress. What's going on here?

Thanks TT2, it was your add to purchased script I was referencing in my original post. I have the link to all your scripts in a safe place in case I want to experiment with any of them. I have one problem though with what you suggest. When I downloaded your script and tried to run it, it asked me to choose a playlist from my device. So, I went into my phone's device sidebar in iTunes and chose the purchased playlist, but it's showing exactly as the one on the computer is showing, and the playlist I created that was supposed to be the one used with your add to purchased script doesn't appear there either. One other thing I'm noticing when I look at the phone version of my playlists is that iTunes shows copying on several of the songs that do show up, despite a sync appearing to be complete. I'm going to try and remove and sync my music again to see if that fixes that issue.

Okay, hopefully this fixes the problem. After accidentally playing a song in my library, the authorization dialog popped up, so I reauthorized my computer and am syncing now. I think the problem was that nothing was actually getting downloaded to my computer. I'm going to try and purchase another song once this is all copied over and see if that downloads as expected. If it does, then I've figured out what the problem was.

Well, I'm not sure what the problem actually was, but things appear to be fixed now in terms of the playlists syncing properly. I purchased a song on my phone Saturday night while it was connected to the computer, and the computer actually downloaded it as I expected it to. Any idea if the other issues I'm having, with certain songs on my device still showing as copying despite a sync being finished, and not syncing voice memos are related to this at all? Also, I have a couple other questions about your scripts, but other than these forums, I don't have a way to contact you.

Have you seen anything official about voice memo syncing? Now that I think about it, it must have been two years ago that it quit working for me, as I was attempting to do some radio work and ended up having to email myself the content I needed. It was two years ago this Christmas I got this laptop which has a decent enough mic for radio. Outside of that, I don't understand how users are expected to get stuff from their phone to their computer.