The setting "Kill miner and try again if mining hasn't started within 60 seconds" is enabled.
I think what could be it in this case, is that the blank window isn't a cgminer.exe process at that moment. Eventhough it says cgminer.exe in the window title.
All the other times I think it works fine I guess.  

I managed to make screenshots this morning.
The CGWatcher log stated: "cgminer closed outside of cgwatcher."

http://tardis1.tinygrab.com/grabs/d81565c15a85db686a8081564355a745789f565365.jpg
http://tardis1.tinygrab.com/grabs/d81565c15a5bc9f4439351984156e78410e103b052.jpg

I've found a simple workaround for the Win 8 & not starting up issue.

Just create a simple bat file "c:\cgwatcher\cgwatcher.exe"  place it in your start up folder (start - run - shell:startup )..works a treat 

Last 3 versions have not worked for me.  I had 1.3.4.3, and it worked great, but 1.3.4.7, 1.3.4,6, and 1.3.4.5 all don't work.  When they launch, everything looks good, but they NEVER start bfgminer.   I get a dos box momentarily that just flashes away, and then CGwatcher says it couldn't start/communicate with bfgminer.  Since 1.3.4.3 is not posted on your site, I had to go back to 1.3.3.3, which works fine.  I tried again going back to any of the above and can repeat the problem.