There's been plenty of posts out there discussing the pros and cons of octopress and other static site generators, so I'm not going to add to the list. I will say that from my personal experience the transition was relatively smooth and that octopress happened to have the necessary features, plugins, and community I needed to get the website I wanted. This certainly may not be the case for everyone, but I am pleased with the overall result so far. Octopress probably does require a bit of web development experience, which I'm fortunate to have. For users without that knowledge base, wordpress is very friendly. However, my needs in a personal webpage are simplistic, and wordpress is just a little too much overkill. It has also become rather mainstream and uses a lot of PHP, which makes it a potential security threat -- especially with a lot of (often shady) plugins. I enjoyed working with vimrepress, but since I'm moving away from wordpress, I won't be developing on it anymore. I did learn something about python-based vim plugins from the experience though.

I wanted a similar vim setup for my new octopress blog. I read another post belaboring this as a lacking feature that ultimately moved them back to wordpress. I was confused by that, since making a decent workflow in octopress is not all that difficult. Here's the steps I took:

nnoremap 'bn :NewPost 
command! -nargs=1 NewPost call NewPost("<args>")
fun! NewPost(args)
   let file = "/web/octopress/source/_posts/" . strftime("%Y-%m-%d") . "-" . tolower(substitute(a:args, " ", "-", "g")) . ".markdown"
   exe "e!" . file
   let g:post_title = a:args
endfun

nnoremap 'bs :SavePost 
command! -nargs=1 SavePost call SavePost("<args>")
fun! SavePost(args)
   let file = "/web/octopress/source/_posts/" . strftime("%Y-%m-%d") . "-" . tolower(substitute(a:args, " ", "-", "g")) . ".markdown"
   exe "w!" . file
   let g:post_title = a:args
endfun

The :NewPost command will allow you to quickly make a new file in the appropriate directory with the appropriate name. The :SavePost command does essentially the same thing except that it uses the buffer you're currently working with instead of making a new one. There might be a better approach than this, but this is just my first go at a solution. Both of the functions set a variable, g:post_title, which I then use in a snipmate snippet file like this:

snippet b
    ---
    date: `strftime("%Y-%m-%d %T")`
    layout: post
    slug: `tolower(substitute(g:post_title, " ", "-", "g"))`
    title: `g:post_title`
    categories:
    - ${1}
    ---

    ${2}

That way I can press ib<Tab> in the new file to get the appropriate front matter. The next thing I wanted was tag and category completion like vimrepress had, so I solved that using these in my ~/.vimrc:

au BufNewFile,BufRead /web/octopress/source/_posts/*.markdown setl completefunc=TagComplete | cd /web/octopress/source
fun! TagComplete(findstart, base)
  if a:findstart
    " locate the start of the word
    let line = getline('.')
    let start = col('.') - 1
    while start > 0 && line[start - 1] =~ '\a'
      let start -= 1
    endwhile
    return start
  else
    let tags = split(system("ls /web/octopress/public/blog/tags"), "\n")
    let cats = split(system("ls /web/octopress/public/blog/categories"), "\n")
    return tags + cats
  endif
endfun

You'll have to change the appropriate directories of course. This allows you to use <C-x><C-u> for tag and category completion and changes the directory automatically when you use the :NewPost command. I might modify these some in the future and update this post, but for now this solution is working for me.