Dont worry about the number of times you have uploaded the file. I have done it myself. Although I'm sure the webmaster would preffer to only have one file to deal with. Your skin will be posted in a few days, can take a week. The webmaster will run the skin for a few days to make sure it's ok before posting it.
If you want to include a preview do so by creating a zip file with the preview within it and post the zip. If you do not the webmaster will do a screen capture of it while he is running it and attach it to your details.
You may want to include versions with your file name. This will allow you to tell the webmaster which is the latest to be posted.
Hope this helps.
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