Hey, another graphic designer! As for Wine different versions work best for different apps. Go to www.winehq.org
and search the App Database for whatever Adobe product you have. The App Database should have everything you need to know to get Photoshop running, however Wine can be very finicky.
There are also some really great open source programs like Gimp and Inkscape. www.osalt.com
is a good source for finding open source versions of programs. Just search (for example) Adobe Dreamweaver and it will give you some good web editors to try. I work at a photography studio and have come to prefer Gimp over photoshop for certain things, however there are just some things that I HAVE to have photoshop for.
Just out of curiosity what exactly do you do? Web design, photography, ect... I might be able to recommend some good apps.
Fonts can be installed pretty easily, can't remember off the top of my head though...
As for your disk space issues, let me give you a warning about NTFS. Every partition has a filesystem which determines how information is stored on the hard drive. Windows always uses NTFS which just shoves files in the first available spot and leaves them there. Because of this you can get large gaps of free space in your drive that make it impossible to shrink the partition.
Example NTFS: (d = data, - = empety)
You may have lots of free space, but because of the little bits of data left way out there near the end, you won't be able to shrink it. Some programs will recognize this and stop before it erases stuff, and others will just delete it. Defragging a hard drive will help consolidate your d's, but they rarely do a very good job (in my opinion) but it's better than nothing.
Linux, on the other hand, uses EXT3 which looks like this:
Much better organized, faster, and completely safe to shrink. So, feel free to tweak your Linux partitions without fear, but whenever shrinking an NTFS (Windows) partition be sure to back up anything you aren't prepared to loose. I would recommend Googling around for a specialized Windows partition editor if you plan on shrinking a lot, since some of those will actually move the stray d's in allowing you to shrink more without loosing data. But, no matter what, it's still a risk.