Some of the hardest tasks related to blogging is getting your off-line blog editor to post to your online store. I tried SquareSpace about a year ago and really loved the offering. The deal breaker for me was that they did not support offline creation of articles and their posting to your site. That changed a while ago and this feature has brought me back. I now publish a number of blogs through this service.
As so no one else has to go through the limited pain of setting up Windows Live Writer to do this, I have the steps listed below in a small tutorial. The assumption is that you have a SquareSpace Blog. see http://www.squarespace.com
Step 1 – Get the “Live” tool set
Window Live Writer is part of the Windows Extensions extensions to windows. Go to http://get.live.com
Programs you can download include:
Additional programs:
Step 2 – Open Write and select “Add blog Account”
The Options drop down has the “Add Blog Account” task.

Step 3 – Select “Other blog service”
SquareSpace is not an out-of-the-box option, select “Other Blog Service”.

Step 4 – Add in your service information
Enter your service information in the next dialog. The Username and Password are the Admin, or user id that you have designated as content creators.

Step 5 – Select Blog Type and Publishing URL
The blog type is “MetaweblogAPI”.

Enter “http://www.squarespace.com/process/service/PostInterceptor”
as the URL that you will deploy your posts to.

At this point, Writer will go to your blog, update the formatting in Write to match the Theme you are using. If you change your settings, colors or scheme, you can re-import those settings
Step 6 – NickName
Give Writer a nickname that you can identify what blog you are writeing to. You can add a number of blogs to the Writer setup and post entries to that blog. This proves great flexibility to both edit your entries in the formatting of that BLOG, but also to publish to multiple blogs from the same instance.

Step 7 – Updating the formatting after changes
As stated above, if you change your blog’s formatting after you import the account, you can update the settings in Writer by selecting “Options” and “Update Account configuration”

Hope this helps. If you have any other software packages that you use to do offline editing, I would live to hear about them in the comments listed below.
Steve Young