Nice site, I like the layout.

A blogging tool will definitely make your site easier to manage in the long term, but if you're tied to that layout (which is understandable) then you're likely to go through some pain in manipulating the CSS to get it to match your site. Another benefit of moving to a blogging tool is that your readers will be able to comment on your posts. That's probably the thing that I enjoy most since moving from static HTML to b2e, getting the feedback from readers.

I've played with several different blogging tools, and in my opinion WordPerfect and b2e are the easiest to manipulate in terms of layout, but it will take some getting used to. If you did all of the CSS work behind your site then you shouldn't have much difficulty in adapting. b2e is my choice between the two, but if you only have one blog then either of them will serve you well.

Regarding starting from scratch vs modifying a pre-existing skin, I would recommend modifying another skin. And with a site layout that is already defined and complex, as yours is, its likely that you'll end up hacking 3 or 4 different skins to get the elements that you like working together.

Let us know what you decide, and when its all done let us know so we can check out your work. Of course, someone is always here if you have questions along the way.

Chris

What I can see looking at your website, the layout isn't that diffucult.
You have a header, and the body is two columns, a sidebar and a 'post' section.

So does most of the evoskins.

I would suggest : start with the evoskin fplanque2000, switch the sidebar from right to left and the post part from left to right.
change the bodybackground image an dthe pageheaderbackgroudn image.
And from that part on, you will see, you almost have already your own site.