I do suggest reducing the size of your picture before you upload them. This is most likely the problem, and it makes uploading them much easier anyway. There is no harm in reducing pictures to be seen on the web because the web cannot display really big pictures very well anyway.
(My guess is that you are tryin to upload very large pictures and the server is just timing out because the process is taking too long. No one ever said technology was easy).
I know this can be a challenge, but most cameras these days can take pictures as big as 13 MB - that can take an ISP a full minute just to upload one picture - depending on your connection.
There are programs that will re-size ALL of your pictures at the same time. One is called Windows Live Photo Gallery.
You go in and you open a folder, select all the pictures. Hit the "edit" tab and select "resize" - you get a dialog box asking where to save them - you want to click on "make new folder" so you are not resizing the originals.
Then resize and save them all to this new folder. I save them as 800 pixels and they upload in no time at all.
Yes - I do this for every picture I upload. It is very important to remember to save them in a different folder, otherwise you are resizing your original pictures.
You can download Windows Live Photo Gallery here:
Windows downloads - Microsoft Windows