
Windows Live Writer from Microsoft is an excellent free tool for blogging. It supports many blogging platforms such as WordPress, Blogger, TypePad, Windows Live Spaces, etc. Its biggest advantage is that you can create and format your blog posts while you’re offline and then directly publish your posts online to your server on your favorite blogging platform. Windows Live Writer handles almost everything for your blog post. One additional advantage of using it is that it can directly and automatically upload the images used in your blog post from your computer to your FTP server when you publish your post on your blog.
If you’ve a self-hosted blog, it is generally advisable to have a separate directory or a sub-domain specifically for storing your images. For example, all images on Tech Superb site are stored in specific separate directories (such as “dir1”) on a separate sub-domain (http://img.techsuperb.com/). For uploading the pictures to such directory or sub-domain, you can use an FTP software (I generally use free and open-source software FileZilla). However, if you’re using Windows Live Writer to prepare and format your posts while working offline (this is what I’ve been doing), it offers you an excellent feature of uploading your images used in a post automatically to your server at the time of publishing your post to your blog through it. You’ve to setup Windows Live Writer for this purpose only once, and thereafter you won’t have to use the FTP software to manually upload your images to your server, Windows Live Writer will do this job for you automatically. What you’d be doing is just to insert the images in your post in Windows Live Writer from your computer, and they will be automatically uploaded to your servers, and moreover, they will be automatically linked correctly from within your post to the image directory and/or sub-domain.
To do so, proceed as under:
(1) Start Windows Live Writer.
(2) Select the blog for which you want to setup auto-uploading of images to your server.
(3) Click the Blog menu, and then click Edit blog settings.
(4) In the Edit Blog Settings dialog box that appears on the screen, from the right sidebar, click on Pictures. Now, from the left pane in the dialog box, select the “Upload pictures to an FTP server” radio button, and then click on Configure FTP button. See the following figure for these settings:

(5) In the “FTP Server Configuration” dialog box that appears on the screen, enter the following relevant information:
See the following figure for these settings:

(6) Now, click OK button twice to close this dialog box and the previous dialog box.
That’s it! Now, your Windows Live Writer has been setup to automatically upload your pictures from your computer to your FTP server at the time of publishing your post to your blog. What you’re required to do is to insert the appropriate pictures from your computer into your post at the relevant places and adjust their settings as per your requirements (such as height, width, alternate text, borders, etc.). The moment you publish the post to your blog, the images used in the post will be automatically uploaded to your FTP server in the folder indicated by you in the above settings and with their existing file names. Moreover, within the text of your post, these images will be automatically linked to the URL path (HTTP) on your online server as set by you above (and not to your local computer path).
Try it yourself. First time you can try it by using the Windows Live Writer feature “Post draft to blog”, so that only a draft is posted to your online blog; this will allow you to confirm whether the images have been correctly uploaded to your server and whether the correct paths have been included automatically.
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I just started using WLW and love the ease of use. BUT…every time I publish an update to a post it uploads basically a duplicate image to my site (adds a number to the image file). Over time this will will not be good from a space perspective. Have you found a work around or fix for this?