Anyone Really Know How to Sync with iTunes

I have used the iPhone and iTunes for quite some time, but one thing continues to aggravate me. I have tried reading across the web for a solution, but I am not finding anything helpful.
First, I have an iPhone 3Gs running Firmware 3.1. I am also running the newest version of iTunes. Second, I actually use two Macs. My office computer is a MacPro and my home computer is a MacBook Pro. Running Snow Leopard on both. As I use both computers quite evenly, sometimes I make iTune store purchases at work and sometimes at home.
The wall I hit is the iPhone doesn't seem to want to sync to multiple computers. Primarily I will use my home MacBook Pro for all of my syncing. But let's say for example, I purchase a movie on iTunes at work. I want it on my iPhone, so I plug it in. I instantly get a message telling me if I want to update my movies on the iPhone, it will erase everything that is already there. Does this mean if I ever want music, tv shows, movies, etc on the iPhone, I need to purchase them from one machine only? It is the same account and verification, so why? I am pulling my hair out.
The other strange thing that happens between the iPhone and iTunes, is I select the iPhone in iTunes, go to TV shows (where I happen to have Season 1 of the Office), and it shows up in iTunes as available. In iTunes, under my iPhone, I check that I want the Office synced to my iPhone. I then sync. The process finishes. I go to the iPod app on the iPhone, and under videos - the Office series is not there! It never tells me I cannot sync it. I can watch the Office on the laptop, but the sync doesn't happen.
I have tried the manual only sync, and that doesn't solve the problem either. Two questions kind of surrounding the same issue. Am I missing something?

MHaddon wrote:
Am I missing something?
Yes, you are. The iPhone can sync iTunes content (music, videos, apps, podcasts, etc.) from only one iTunes library at a time. If you try to sync content from another iTunes library, iTunes will erase the content from the first computer. It doesn't matter if you have the same iTunes account on both computers or not.
You can use a external HD or a flash drive (or even an older iPod) to move your purchases from one computer to the other (your primary iPhone sync computer). This explains how: iTunes for Mac - How to copy purchases between computers: http://support.apple.com/kb/HT1373

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