Hi The_Daily_Bugle,
I'm not sure if I understand every point you are trying to make clearly but...
You can use the same image multiple times within your item description. The easiest way to add images directly into your item description, which doesn't require the use of html, is to place them in the editor using the Freetiva Image button on the lower right of the editor toolbar(it has an icon of a mountain and sun on it). You should also be able to place the same image in same listing multiple times if you are referencing the images using html.
I don't believe it is Auctiva bandwidth problems that are causing your listings to crash...it is most likely being caused by some interference by an application or setting on your system. I just tested this out and I was able to use the same image multiple times in the same listing without encountering any problems.
There was also a short period today during which we were experiencing problems with one of our image servers. The fact that you saw red x's in place of your images was most likely due to that issue.
If you are concerned that it is taking you too long to create listings using Auctiva, I definitely recommend using profiles, which can greatly increase your listing efficiency. There are recorded classes and interactive tutorials that go over the set up and use of profiles available on the following link: http://www.auctiva.com/help/tutorials.aspx
For further assistance with this matter, I suggest filing a support request using the appropriate link on our help page:
http://www.auctiva.com/free_auction_software_help/help.aspx
-Mike