Don't store your wine directory on an ntfs partition.
you might be able to get it to work but it will cause you to go bald from stress within three months. Put it on a sane file system like ext3 or reiserfs. incidently there is a third party file system driver for windows that will let you mount and read/write an ext3 file system. I forget what the software is, but a little googling for terms like "windows" and "ext3" should find it in quick order.
As to the updating section those questions are specific enough to a single distrobution (Ubuntu) that it makes more sense to bring those questions to a forum that caters to the distribution (like the ubuntu forums) than to a general site like USALUG. Or so I think anyway.
Thats not to say we won't try our darndest to help you of course. we'll always try to help.
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ArchLinux x86_64 - Custom Built Desktop
ArchLinux x86_64 - Compaq CQ50 Laptop
ArchLinux i686 - Acer Aspire One Netbook
ArchLinux i686 - Dell Presario ze2000 (w/ shattered LCD)
PuppyLinux, CloneZilla, PartedMagic, DBAN - rescue thumbdrives
Windows 7 (x86_64 desktop alternate boot)