Technical Help

So now I am on holiday I have decided to sort a few things out. And many of them I am not sure how to do, or the best way to go about them, or if some of them are even possible.

So would like some help / pointing in the right direction.

1. Emails.

I have several email accounts and am getting fed up of checking them all, so I have thought about using Outlook or something similar to kind of group them all together.

Is this wise? Any known issues with doing this?

With outlook, can I create an 'account' that includes all my 5 or 6 email addresses, and I can log into any PC and check them all using outlook?

What do I do when I change my operating system to Windows 7 in a short while. Is there a way of saving all my downloaded emails/contacts/calender and just transferring the files without having to set it all up again?

2, Contacts + Calender.

I am going to restore my iphone to factory settings (many many issues that I am hoping will fix themselves), so I have saved all my iphone contacts to outlook (it was empty, so seemed like the best place), is there a way to merge the numbers I now have in outlook with the email addresses from Gmail, and then put them back onto my iphone?

Is google calender better than outlook calender? (re. syncing with iphone etc.)

3, I now have a domain. joshjgordon.com and I am finally going to put something there (not entirely sure what yet, probably this blog and some other stuff). I hear wordpress is good for the blog side of things, is there a good program to use for other non-blog stuff?

Could someone point me in the direction of a good FAQ / Tutorial for web design etc. I have never done it really before.

4, Why does outlook only download 270 (out of several thousand) of my emails at once. It is rather annoying, has taken me for ever to get up to march 2009 (started feb 09, when I first set up outlook and have since ignored)

5, Andy, what app do you use to do your contacts? They look pretty snazzy.

Cheers Y'All. More questions later, probably.