I'm sorry to hear about all the computer woes, Watson! Get the Mac.
1) I bought my Mac when I hadn't used one either. Initially, I got it because I knew that if I bought a PC I would waste tons of times modifying it/playing games/etc and wanted something PURELY for school. Yes, there is a learning curve but once you get used to that it becomes just as comfortable to use as any computer.
2) My last PC notebook got taken down HARD (read: completely unusable) not because I wasn't careful but because I logged on to a network at a school where someone else wasn't careful and the virus trotted over to my computer and killed it. Security is a major downside for the PC, though I've heard rumors that Windows 7 is supposedly better about this. Nevertheless, since then I've had 3 Macs and not a single virus or security issue regardless of network usage. Also, no proprietary software to install either - which is nice.
3) Supposedly Mac has the reputation for being the Audio/Video computer with PC having the reputation for being the Business/Office machine but with the transferability of software and the wide range of options out there, I'm not sure that today there's a huge difference.
4) Most definitely yes - office files are cross compatible (as are most software files like .psd .pdf etc). That said, Office Mac has been the cause of most of my software woes with this computer, so they have a ways to go before they iron out all the wrinkles. For some reason Office demands a LOT from the Mac when it's running which can cause slowdowns and such.
5) The cheapest Mac to the best of my knowledge is the Mini which, if I recall correctly, is about $599. Personally, I've had an iBook (that I purchased off of Ebay out of warranty), and a Powerbook G4 (the old Macbook Pro) and a standard white Macbook from the store. Apple offers a student and a military discount so if someone in your family fits those categories, it may work to your benefit to have them pay the bill at the store.
Overall, they're great machines. They have problems as well - I've had crashes that have been DEVASTATING on my Mac but they all occurred as a result of attempting to dual-boot Windows, so interpret that as you will.
I've had my current Macbook for 3 years with the extended warranty and haven't had a single hardware issue with it. The "e" key fell off my Powerbook at one point and they had to replace the entire keyboard and the white plastic top case did crack quite frequently on the Macbook which was also replaced on several occasions. So, I'd categorize most of my problems as purely cosmetic. It can still be annoying to drag the computer in for repair though, especially if you don't live near an Apple retail location.
Regarding warranty and resale, another nice feature is that Macs tend to hold resale value. If you purchase the three year warranty, you can turn around the computer and sell it, say, a month before the warranty expires which adds quite a bit to its ultimate value. People tend to see that as an extra "insurance policy" in case you're trying to sell them a lemon or something.
Worst case scenario is that you have to sell your computer for parts, but even then there's still a good market for Mac parts. For example, when the logic board on my iBook eventually went, it still sold for a few hundred on Ebay for parts.
Hope this helps and that everything goes well for you from now on computer-wise!
It's not hard, but might be a slight adjustment to get used to where things are.
