Hello,
1) It does not automatically (after upload) add annotations. You need to manually do that (right click on the video or videos and click on Add Annotations) AFTER the video is 100% processed on YouTube. But you can select multiple videos at a time when adding annotations (they just need to be processed on YouTube).
2) I will see what I can do about adding that feature
3) It's specs are good. Make sure that .net framework 4.0 is installed.
Thanks,
Vlad