I’m not a WordPress expert but will share my own experiences: I had a problem with pictures not uploading too. One of the problems that I had was uploading pictures with spaces in between, such as “john aberle at park.jpg” – I had to rename it “john_aberle-at_park.jpg” to get WordPress to recognize it.
As my site is on Yahoo! Small Business Web Hosting and I’m on WordPress version 2.6, I don’t know if the rest of this works exactly the same for you, but here’s what I do.
I go to Write then to Post. On the Write Post page for creating a new post, in the Post section where you write your article, between the word Post and the Visual / HTML tabs is “Add Media” followed by several icons. The first one is the “Add an Image” icon for adding a picture.
When I click on that, it takes me to a page that offers two choices: “From Computer” and “From URL.” Even though I had already uploaded the image into my blog’s …/wp-admin/images folder, I found it easier to use From Computer where I used the
to select the picture again from off my hard drive.
If you need more help than that, you might want to contact Cathy Perkins, the WordPress Wizard at https://tinyurl.com/d8vjm4, as she can help you get a picture into your sidebar using a Text Widget.