Windows Live Writer has this excellent facility to upload images without having to use a separate FTP program. You can insert images into your WordPress blog posts (or any blogging software that can be managed through Windows Live Writer) just like you do in, say, MS Word, and when you publish the blog post, the image is automatically uploaded to the designated folder where you are hosting your WordPress blog.
In order to upload your images through Windows Live Writer, load it, click Blogs and then click the blog for which you would like to automatically upload images. Then again click on Blogs, and this time, click Edit blog settings…. You are presented with this screen:
When you click Pictures, you get this:
You select the radio button “Upload pictures to an FTP server” and click the “Configure FTP…” button.
The above window is just like using an FTP program to log into your FTP account. Enter the required information: FTP host name, user name and password, and then click the button that is surrounded by the red border. Here you will be able to select the actual remote server where you want Windows Live Writer to upload the images. The last box needs to be filled manually. Here you have to enter the URL of your images folder. Suppose your images folder is called “photos” and it resides in the root folder, it’s URL is going to be http://yourblogdomain.com/photos/.
Click OK and you’re done. After this whenever you want to insert an image into a blog post that you are currently preparing or editing, simply click the insert image icon present in the top bar: