can i use wordpress to redo my site?

I’m tired of updating my website by hand, and want to know if I can use wordpress easily to maintain it. The url is artfusionstudio.com. I intend to keep the same look (removing the frames though). My main concerns are:

1) making the image uploading easy – I have thumbnails of the image which links to the full post which has the larger image and some text. Can I do this in one step in wordpress? Or will I need to resize images manually, and how will I get the thumbnail to appear for the placeholder, and the big image to appear in the main post.

2) I have major categories (glass, acrylic, etc.) with subcategories (bowls, plates, vases, etc.) Can wordpress easily support this?

3) Making the transition as easy as possible, what steps or extensions do I need?

Thanks for any help to a wordpress newbie, I think this is going to work great, but I want to make sure I’m not missing anything before I spend lots of time learning only to find out it can’t do a critical thing I need.

Thanks!