It has nothing to do with permissions, and everything to do with trying to save a file that's effectively streaming from an app in your computer. If you can't get the internet and DropBox to behave like an internal drive - which you can't - then the handshaking delays will rapidly cause the save process to time out. Uploading a file, on the other hand, uses a different protocol which is much more tolerant of timing errors/delays in the handshaking.
I'm not surprised that .sesx files will upload directly - they are much smaller, and when they are exported they are already saved files (which your streamed MP3 isn't).
AS for stability of your internet connection - well yours might be stable (mine certainly is) but the DropBox connection certainly isn't, and that's where the streaming errors occur. If you monitor the feed, you can see it happening - it uploads fine for a while, and then suddenly stops - which is generally when the crashes happen. The bottom line is that it's always safer to upload a saved file - apart from anything else, that's far less likely to have errors in it.
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