1. as others have mentioned before MacOSX's TextEdit will read and save MS Word documents just fine. But it is a basic application like Wordpad on Windows. For full blown functionality use MS Office 2004 for Mac or MS Office via Bootcamp or Parallels.
2. i can understand that switching everyone else to Skype might not be the most favourable, even though it is on of the best chat/ audio/ video/ voip/ voip -> phone applications out there. but if you need to audio/ video chat on MSN, no questions ask, you will need to use MS MSN under Windows. it will work under Bootcamp and Parallels.
3. yes, just make sure you buy the right adapter when you purchase
4. considering your needs above, i suggest the two options of Bootcamp and/ or Parallels. You also can resort to VM Fusion or Crossover. Though, former is more aimed at the professional server market and lacks the tight & friendly Windows integration of Parallels, and, ladder is a bit of a gamble with newer application. I also have no idea if the Mac's webcam is supported in Crossover.
Bootcamp: make sure you have WXP SP2 (!!). Anything below won't do it. Home or Professional are both okay though. You will need to start your new Mac into OSX, download the Bootcamp from the Apple website, start the application and just follow the instructions. Make sure you parition the amount of drive space for WXP as you need it. The rest is pretty straight forward. Tip; During the driver installation under XP be patiened and let it do its job. Some drivers need a while and it is better not to interfere with the hardware dialogues popping up.
The drawbackis that you can only run one OS at the time. You will need to reboot to start the other.
Parallels: is an application which will illusion Windows that it is running on an very ordinary PC. It runs with almost any version though WXP is probably most support, integration wise. You can download the free trial from the Parallels website. Install it, start it up, and use the wizard to make you basic Windows install. After Windows started up Parallels will install a set of drivers and tools which will integrate WXP very nicely into your MacOSX (i.e. drag&drop, copy&paste, folder sharing, network sharing, and , probably the best feature, coherence mode). Mounting a floppy drive into WXP under parallels should also be of no problem. Once the newest version MSN is installed you will also be able to use the Mac's build-in iSight webcam.
The drawback is that your Windows performance for such things as games or other heavily CPU or graphics demanding applications might not be ideal. However, for such tasks as Office apps, MSN, internet browsing, you'll barely notice any slowdown. it will just be a bit more normal PC than the performance your new Mac actually could deliver
Bootcamp + Parallels: basically, you can instruct Parallels, instead of creating a virtual hard drive, to use your already installed Bootcamp partition. This will give you the choice of both worlds in case you will need full windows power occasionally.
5. Regular USB drives should work out of the box under MacOSX and WXP. You also might just take your current drive and a floppy down to your Mac shop and test it. If for some weird reason you current drive will not work, there are plenty of cheap choices..
Enjoy