ASP Upload Image Hangs (yes, I've scoured the forums)

I see this issue posted a lot with a number of different solutions. I've turned the code upside-down and diagonal and can't figure out what's wrong. After everything, I started from scratch and went through and made the most sensible changes to the code to make sure I hadn't messed something up along the way- to no avail.

Problem:
1. Click the "Insert/Edit Image" Button
2. Select the "Upload" tab
3. Browse to test image on my local (small file size)
4. Click "Send it to Server"

It hangs on that horizontal brown status bar forevvver.

Currently I'm working with the last stable release- 2.6.3 (I've tried the beta and the nightly).

Outside of that, the only thing that I've modified is:
\fckeditor\editor\filemanager\connectors\asp\config.asp

I created the folder structure so it fits the file path:
ConfigUserFilesPath = "/userfiles/"

I set ConfigIsEnabled = true

I read a post that made me question how these paths should be set: (this one doesn't work)

ConfigFileTypesPath.Add "Image", ConfigUserFilesPath & "image/"
ConfigFileTypesAbsolutePath.Add "Image", ""
ConfigQuickUploadPath.Add "Image", ConfigUserFilesPath
ConfigQuickUploadAbsolutePath.Add "Image", ""