New iPod Touch, Can't get iTunes to work, extra headaches

Hello,
This is my first day in the Apple world: I caved and thought it would be good to get a new mp3/video player after my last one died. I ended up getting a 4th Gen Black iPod Touch - not sure if the color matters, but why not?
Anyway, my second problem (first being the weird packaging, of tape through plastic then stuck on) started with iTunes: the thing just would NOT download. Every time I tried, the website kept saying "There is a problem with this Windows Installer package. A program required for this install to completecould not be run. Contact your support personnel or package vendor." That's just great: I can't get any music or video ONTO my iTouch without iTunes...right?
After browsing around I found an older version of iTunes that seemed to work. Yay! But not really. Nobody ever mentioned that .flac and .avi files can't be imported into iTunes at all...so I had to go hunting online for third party converters. This took care of THAT problem...
However, now that conversion is up, the older version of iTunes won't pick up my iPod Touch and Sync it. There is actually a "Sync iPod" button under "File" tab, but it's grayed out and I can't use it.
Not entirely sure if this is why, but according to a few people, when a new iTunes comes out, the older one stops functioning as fully as it originally did, forcing people to upgrade their iTunes in order to make it work like normal.
I tried to find a third party program to pick up my iPod Touch so I could upload files, but no luck. I feel like an idiot for not knowing how to turn source code into a program, and the binary installers I did find were user-hostile (ie. Right clicking to bring up a menu actually plays the movie and there's no stop button, you have to end task from the task manager). Windows Explorer only shows one folder in my iPod Touch, which is empty and four letters long, which gives no clue as to what it is.
So here's my big question: now that I finally am fully ready to upload my files to my iPod Touch, I can't. Why?
Is it my version of iTunes? Why can't I download iTunes' newest version? Why does updating from the older version yield the same result (though I'm sure both installers are the same)? Is there another way to get all my media onto my device?
Thanks in advance...talk about a four hour headache...

I've used the Reset Network Settings feature in my iPod Touch after every failed attempt to connect to my wireless network. I've also reset the wireless access point and router after making changes to them.
It appears that my Touch is finding the wireless network, accepting the security password/key, and connecting to the wireless access point and router (I get a full signal on the strength indicator). However, the Touch appears to be acquiring the IP Address automatically, right? Thus, it gets the IP Address starting with "169". If I can manually set up the TCP/IP settings, I believe I can get it to connect. Is there a way to set up the TCP/IP settings manually?

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I had a version 1.1.4 iPod Touch for several days and it worked quite well. I was able to automatically connect to wireless connections at work, at home and at my parents house without meddling with any wireless settings and by just using DHCP.
The other day I exchanged the iPod Touch for a different one, due to a defect in the case manufacturing, and with this iPod Touch, I haven't been able to connect to any of the previously mentioned wireless networks. I noticed that I wasn't able to get an IP address at all at my parents house, but I figured it was because I hadn't upgraded to 1.1.4, and was still at 1.1.3. I upgraded to 1.1.4 though this morning and at the work network, I'm having the same issue. I can easily connect to the wifi networks, but if I look at the DHCP settings, it's all blank. I can't get an IP address.
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New iPod Touch, Can't get iTunes to work, extra headaches

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