The advanges of getting multiple different links seems good for PR, if you choose you are in the right category. On the other hand, Microsoft doesn't seem to be pushing the Directory much. There is no obvious link to it from the MSN home page or from the new Microsoft tool bar.
I bought it, cheap link deal if you ask me. Search the forums, there's a miles long thread on this Directory already with all pro's and features discussed in-depth.
Even at a yearly fee it's a great directory to get in. You get links to some of your other pages and it's all for about $4.00 a month. I hvae a few sites listed and most of my links are on PR5 & PR4 pages.
You can get in multiple categories and they put me exactly where I wanted to be with exactly the anchor text I wanted, which is a huge plus.
Seems like a concensus. The PR is worth the price of admission. Much better deal than Yahoo Directory.