two problems syncing my phone

Hi all,

I'm having two problems with my phone currently:

1. The last two times I've had to update, I've done so via iTunes. Although the update process works flawlessly, my phone keeps prompting me that there are items on my phone that have not been transfered to my computer, and prompts me to transfer them. It does this despite syncing multiple times. How can I fix this?

2. Because of problem #1 above, I decided to start syncing my podcasts from iTunes. It turns out that for whatever reason, iTunes kept a bunch of old podcasts in my library that were no longer in their respective feeds, or that I had played long ago, so after clearing those up, all seemed fine until I started playing new episodes. There doesn't seem to be any rhyme or reason to when the following problem happens, but I want to keep it from ever happening, as it's getting rather annoying. When a new episode comes in, it appears as an unplayed episode, as it should. I play it, and it disappears from the listen now tab, also as it should. However, next time I sync to iTunes, sometimes said episode will reappear, despite the app telling me that I've recently played it. The only way I've found to completely get rid of the file is to first go into where the podcast file is stored on my computer and delete it manually, and then sync my phone to get it off of there. Then I usually have to go in and remove it from my library. Is there some way I can make sure I never have to do the above steps? It shouldn't be syncing old podcast episodes ever. Also a more minor problem but still probably a bug, sometimes iTunes doesn't delete old episodes.